N-bromobutanimide → Tert-butyl 4-(3-bromo-2-oxopropyl)piperidine-1-carboxylate

HRID 335259노트

반응식

HRID 335259 반응식
C[Si](C)(C)[O:3][C:4](=[CH2:19])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1.C(=O)(O)[O-].[Na+].[Br:27]N1C(=O)CCC1=O>C1COCC1>[Br:27][CH2:3][C:4](=[O:19])[CH2:5][CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1

참가 물질

5

반응물 3

HCID 67184N-bromobutanimideHCID 516892Sodium BicarbonateHCID 66994845Tert-butyl 4-(2-(trimethylsilyloxy)allyl)piperidine-1-carboxylate

생성물 1

HCID 22243583Tert-butyl 4-(3-bromo-2-oxopropyl)piperidine-1-carboxylate수율 110%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  1. customPartitioned between ether (150 mL) and saturated sodium bicarbonate
  2. washThe combined organic layers were washed with saturated bicarbonate, brine
  3. customdried
  4. concentrationconcentrated

출처 및 근거

ORD 기록
ord-b6a96567cc93453095c43d430fa080d7
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883828B2

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