1-Bromo-2-propanol → tert-Butyl (1-(2-hydroxypropyl)piperidin-4-yl)carbamate

HRID 1257745노트

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HRID 1257745 반응식
[C:1]([NH:8][CH:9]1[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH:15][CH:16]([CH3:19])[CH2:17]Br>C(C#N)(C)=O>[C:4]([O:3][C:1](=[O:2])[NH:8][CH:9]1[CH2:14][CH2:13][N:12]([CH2:17][CH:16]([OH:15])[CH3:19])[CH2:11][CH2:10]1)([CH3:7])([CH3:6])[CH3:5]

참가 물질

4

반응물 2

HCID 297401-Bromo-2-propanolHCID 7238334-(N-Boc-amino)piperidine

생성물 1

HCID 56973353tert-Butyl (1-(2-hydroxypropyl)piperidin-4-yl)carbamate수율 59%

시약·촉매·용매 1

HCID 694302-Oxopropiononitrile용매

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온도
60 °C

실험 절차

A mixture of 4-(N-Boc-amino)-piperidine (1.0 g, 5.0 mmol), 2-hydroxybromopropane (1.0 g; 7.5 mmol) and TEA (0.76 g, 7.5 mmol) in AcCN (20 mL) was heated at 60° C. for 4 days. The reaction mixture was partitioned between EtOAc and water. The organic layer was separated, washed with brine, dried over Na2SO4 concentrated under reduced pressure. Purification of the residue by column chromatography on silica (0-5% 2M ammonia-MeOH in DCM) afforded [1-(2-hydroxy-propyl)-piperidin-4-yl]-carbamic acid tert-butyl ester (0.76 g, 59%) as an oil. LCMS (Method G; ESI): RT=0.49 min, m+1=259.3.

후처리

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customPurification of the residue by column chromatography on silica (0-5% 2M ammonia-MeOH in DCM)

출처 및 근거

ORD 기록
ord-3e180069ac294000a1dfcc63fe2a63b2
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461328B2

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