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CC(C)(C)OC(=O)N1CCC(CC1)CC(=O)CBr製品情報
Tert-butyl 4-(3-bromo-2-oxopropyl)piperidine-1-carboxylate (CAS 473795-43-6) product identity, structure identifiers and related reaction data for chemical intermediate research and sourcing review.
想定用途
専門的研究・工業用途限定
データベース ID 22243583
安全上の注意
For professional research and industrial use only. Review the supplier safety data sheet before handling.
合成データ
12 反応 · 12 文献
反応条件: temp:0.00; pressure:0.00; stir:
ソース ID: ord-afa1fddfe57147f0bf3a03a5963ad41e反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
実験手順: Heated a mixture tert-butyl 4-(3-bromo-2-oxopropyl)piperidine-1-carboxylate (1.38 g, 4.32 mmol), 1-(5-bromo-3-phenoxypyridin-2-yl)thiourea (1.0 g, 3.08 mmol), triethylamine (0.731 mL, 5.24 mmol), and ethanol (50 mL) at reflux overnight. Cooled to ambient temperature and partitioned between into water and ethyl acetate. Washed the organic layer with water, brine, dried and concentrated. Purified by MPLC (Biotage) eluting with 3:1 hexane:ethyl acetate to afford the title compound (1.54 g, 92%) as a white powder: 1H NMR (CDCl3) δ 8.66 (s, 1H), 8.13 (s, 1H), 7.43 (t, 2H), 7.25 (t, 1H), 7.12 (s, 1H), 7.06 (d, 2H), 6.45 (s, 1H), 4.08 (m, 2H), 2.67 (m, 2H), 2.56 (d, 2H), 1.85 (m, 1H), 1.66 (m, 2H), 1.44 (s, 9H), 1.15 (m, 2H). at reflux overnight partitioned between into water and ethyl acetate Washed the organic layer with water, brine dried concentrated Purified by MPLC (Biotage) eluting with 3:1 hexane
ソース ID: ord-127a84dc9e044eb08356b51b7fda89cf反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
実験手順: To a solution of tert-butyl 4-(2-(trimethylsilyloxy)allyl)piperidine-1-carboxylate (6.43 g, 20.5 mmol) in THF (100 mL) at 0° C. was added sodium bicarbonate (2.58 g, 30.7 mmol) followed by 1-bromopyrrolidine-2,5-dione (3.65 g, 20.5 mmol). Warmed to ambient temperature and stirred 90 minutes. Partitioned between ether (150 mL) and saturated sodium bicarbonate. The aqueous layer was reextracted with ether (100 mL). The combined organic layers were washed with saturated bicarbonate, brine, dried, and concentrated to afford the title compound (7.2 g, 110% yield) as a yellow oil. Purity was 85% with the major impurity being succinimide. The crude material was used in the next step. Partitioned between ether (150 mL) and saturated sodium bicarbonate The combined organic layers were washed with saturated bicarbonate, brine dried concentrated
ソース ID: ord-b6a96567cc93453095c43d430fa080d7反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
実験手順: Heated a mixture tert-butyl 4-(3-bromo-2-oxopropyl)piperidine-1-carboxylate (1.38 g, 4.32 mmol), 1-(5-bromo-3-phenoxypyridin-2-yl)thiourea (1.0 g, 3.08 mmol), triethylamine (0.731 mL, 5.24 mmol), and ethanol (50 mL) at reflux overnight. Cooled to ambient temperature and partitioned between into water and ethyl acetate. Washed the organic layer with water, brine, dried and concentrated. Purified by MPLC (Biotage) eluting with 3:1 hexane:ethyl acetate to afford the title compound (1.54 g, 92%) as a white powder: 1H NMR (CDCl3) δ 8.66 (s, 1H), 8.13 (s, 1H), 7.43 (t, 2H), 7.25 (t, 1H), 7.12 (s, 1H), 7.06 (d, 2H), 6.45 (s, 1H), 4.08 (m, 2H), 2.67 (m, 2H), 2.56 (d, 2H), 1.85 (m, 1H), 1.66 (m, 2H), 1.44 (s, 9H), 1.15 (m, 2H). at reflux overnight partitioned between into water and ethyl acetate Washed the organic layer with water, brine dried concentrated Purified by MPLC (Biotage) eluting with 3:1 hexane
ソース ID: ord-b6d03f027ddb40868168c42928b0acaf反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
実験手順: Heated a mixture tert-butyl 4-(3-bromo-2-oxopropyl)piperidine-1-carboxylate (1.38 g, 4.32 mmol), 1-(5-bromo-3-phenoxypyridin-2-yl)thiourea (1.0 g, 3.08 mmol), triethylamine (0.731 mL, 5.24 mmol), and ethanol (50 mL) at reflux overnight. Cooled to ambient temperature and partitioned between into water and ethyl acetate. Washed the organic layer with water, brine, dried and concentrated. Purified by MPLC (Biotage) eluting with 3:1 hexane:ethyl acetate to afford the title compound (1.54 g, 92%) as a white powder: 1H NMR (CDCl3) δ 8.66 (s, 1H), 8.13 (s, 1H), 7.43 (t, 2H), 7.25 (t, 1H), 7.12 (s, 1H), 7.06 (d, 2H), 6.45 (s, 1H), 4.08 (m, 2H), 2.67 (m, 2H), 2.56 (d, 2H), 1.85 (m, 1H), 1.66 (m, 2H), 1.44 (s, 9H), 1.15 (m, 2H). at reflux overnight partitioned between into water and ethyl acetate Washed the organic layer with water, brine dried concentrated Purified by MPLC (Biotage) eluting with 3:1 hexane
ソース ID: ord-b6d03f027ddb40868168c42928b0acaf反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
実験手順: To a solution of tert-butyl 4-(2-(trimethylsilyloxy)allyl)piperidine-1-carboxylate (6.43 g, 20.5 mmol) in THF (100 mL) at 0° C. was added sodium bicarbonate (2.58 g, 30.7 mmol) followed by 1-bromopyrrolidine-2,5-dione (3.65 g, 20.5 mmol). Warmed to ambient temperature and stirred 90 minutes. Partitioned between ether (150 mL) and saturated sodium bicarbonate. The aqueous layer was reextracted with ether (100 mL). The combined organic layers were washed with saturated bicarbonate, brine, dried, and concentrated to afford the title compound (7.2 g, 110% yield) as a yellow oil. Purity was 85% with the major impurity being succinimide. The crude material was used in the next step. Partitioned between ether (150 mL) and saturated sodium bicarbonate The combined organic layers were washed with saturated bicarbonate, brine dried concentrated
ソース ID: ord-4e40dc63623d47838abd4d046c864aa3反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
実験手順: Heated a mixture tert-butyl 4-(3-bromo-2-oxopropyl)piperidine-1-carboxylate (1.38 g, 4.32 mmol), 1-(5-bromo-3-phenoxypyridin-2-yl)thiourea (1.0 g, 3.08 mmol), triethylamine (0.731 mL, 5.24 mmol), and ethanol (50 mL) at reflux overnight. Cooled to ambient temperature and partitioned between into water and ethyl acetate. Washed the organic layer with water, brine, dried and concentrated. Purified by MPLC (Biotage) eluting with 3:1 hexane:ethyl acetate to afford the title compound (1.54 g, 92%) as a white powder: 1H NMR (CDCl3) δ 8.66 (s, 1H), 8.13 (s, 1H), 7.43 (t, 2H), 7.25 (t, 1H), 7.12 (s, 1H), 7.06 (d, 2H), 6.45 (s, 1H), 4.08 (m, 2H), 2.67 (m, 2H), 2.56 (d, 2H), 1.85 (m, 1H), 1.66 (m, 2H), 1.44 (s, 9H), 1.15 (m, 2H). at reflux overnight partitioned between into water and ethyl acetate Washed the organic layer with water, brine dried concentrated Purified by MPLC (Biotage) eluting with 3:1 hexane
ソース ID: ord-127a84dc9e044eb08356b51b7fda89cf反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
実験手順: To a solution of tert-butyl 4-(2-(trimethylsilyloxy)allyl)piperidine-1-carboxylate (6.43 g, 20.5 mmol) in THF (100 mL) at 0° C. was added sodium bicarbonate (2.58 g, 30.7 mmol) followed by 1-bromopyrrolidine-2,5-dione (3.65 g, 20.5 mmol). Warmed to ambient temperature and stirred 90 minutes. Partitioned between ether (150 mL) and saturated sodium bicarbonate. The aqueous layer was reextracted with ether (100 mL). The combined organic layers were washed with saturated bicarbonate, brine, dried, and concentrated to afford the title compound (7.2 g, 110% yield) as a yellow oil. Purity was 85% with the major impurity being succinimide. The crude material was used in the next step. Partitioned between ether (150 mL) and saturated sodium bicarbonate The combined organic layers were washed with saturated bicarbonate, brine dried concentrated
ソース ID: ord-b6a96567cc93453095c43d430fa080d7反応条件: temp:0.00; pressure:0.00; stir:
ソース ID: ord-afa1fddfe57147f0bf3a03a5963ad41e反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
実験手順: Heated a mixture tert-butyl 4-(3-bromo-2-oxopropyl)piperidine-1-carboxylate (1.38 g, 4.32 mmol), 1-(5-bromo-3-phenoxypyridin-2-yl)thiourea (1.0 g, 3.08 mmol), triethylamine (0.731 mL, 5.24 mmol), and ethanol (50 mL) at reflux overnight. Cooled to ambient temperature and partitioned between into water and ethyl acetate. Washed the organic layer with water, brine, dried and concentrated. Purified by MPLC (Biotage) eluting with 3:1 hexane:ethyl acetate to afford the title compound (1.54 g, 92%) as a white powder: 1H NMR (CDCl3) δ 8.66 (s, 1H), 8.13 (s, 1H), 7.43 (t, 2H), 7.25 (t, 1H), 7.12 (s, 1H), 7.06 (d, 2H), 6.45 (s, 1H), 4.08 (m, 2H), 2.67 (m, 2H), 2.56 (d, 2H), 1.85 (m, 1H), 1.66 (m, 2H), 1.44 (s, 9H), 1.15 (m, 2H). at reflux overnight partitioned between into water and ethyl acetate Washed the organic layer with water, brine dried concentrated Purified by MPLC (Biotage) eluting with 3:1 hexane
ソース ID: ord-ec7b7e3b6b0f460ea9bf008baeb6e0e7反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
実験手順: To a solution of tert-butyl 4-(2-(trimethylsilyloxy)allyl)piperidine-1-carboxylate (6.43 g, 20.5 mmol) in THF (100 mL) at 0° C. was added sodium bicarbonate (2.58 g, 30.7 mmol) followed by 1-bromopyrrolidine-2,5-dione (3.65 g, 20.5 mmol). Warmed to ambient temperature and stirred 90 minutes. Partitioned between ether (150 mL) and saturated sodium bicarbonate. The aqueous layer was reextracted with ether (100 mL). The combined organic layers were washed with saturated bicarbonate, brine, dried, and concentrated to afford the title compound (7.2 g, 110% yield) as a yellow oil. Purity was 85% with the major impurity being succinimide. The crude material was used in the next step. Partitioned between ether (150 mL) and saturated sodium bicarbonate The combined organic layers were washed with saturated bicarbonate, brine dried concentrated
ソース ID: ord-08bbcc5a27cb45d696916d14b0ad4305反応条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.
実験手順: Heated a mixture tert-butyl 4-(3-bromo-2-oxopropyl)piperidine-1-carboxylate (1.38 g, 4.32 mmol), 1-(5-bromo-3-phenoxypyridin-2-yl)thiourea (1.0 g, 3.08 mmol), triethylamine (0.731 mL, 5.24 mmol), and ethanol (50 mL) at reflux overnight. Cooled to ambient temperature and partitioned between into water and ethyl acetate. Washed the organic layer with water, brine, dried and concentrated. Purified by MPLC (Biotage) eluting with 3:1 hexane:ethyl acetate to afford the title compound (1.54 g, 92%) as a white powder: 1H NMR (CDCl3) δ 8.66 (s, 1H), 8.13 (s, 1H), 7.43 (t, 2H), 7.25 (t, 1H), 7.12 (s, 1H), 7.06 (d, 2H), 6.45 (s, 1H), 4.08 (m, 2H), 2.67 (m, 2H), 2.56 (d, 2H), 1.85 (m, 1H), 1.66 (m, 2H), 1.44 (s, 9H), 1.15 (m, 2H). at reflux overnight partitioned between into water and ethyl acetate Washed the organic layer with water, brine dried concentrated Purified by MPLC (Biotage) eluting with 3:1 hexane
ソース ID: ord-b6d03f027ddb40868168c42928b0acafPubChem References
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