2-Bromoethanol → Methyl(3S,4R)-4-{[(benzyloxy)carbonyl]amino}-1-(2-hydroxyethyl)piperidine-3-carboxylate

HRID 1644312노트

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HRID 1644312 반응식
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[CH2:17][CH2:16][NH:15][CH2:14][C@@H:13]1[C:18]([O:20][CH3:21])=[O:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.Br[CH2:32][CH2:33][OH:34]>C(#N)C>[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[CH2:17][CH2:16][N:15]([CH2:32][CH2:33][OH:34])[CH2:14][C@@H:13]1[C:18]([O:20][CH3:21])=[O:19])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 108982-BromoethanolHCID 81531DiisopropylethylamineHCID 58999552methyl (3S,4R)-4-{[(benzyloxy)carbonyl]amino}piperidine-3-carboxylate

생성물 1

HCID 66774341Methyl(3S,4R)-4-{[(benzyloxy)carbonyl]amino}-1-(2-hydroxyethyl)piperidine-3-carboxylate

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
70 °C

실험 절차

A mixture of methyl(3S,4R)-4-{[(benzyloxy)carbonyl]amino}piperidine-3-carboxylate (WO 2005/066176) (2.29 g, 7.83 mmol), N,N-diisopropylethylamine (2.05 mL, 11.75 mmol and 2-bromoethanol (0.722 mL, 10.18 mmol) in dry acetonitrile (17 mL) was heated in the microwave at 70° C. for 4.5 hours. The solvent was removed under reduced pressure and the residue taken up in ethyl acetate (200 mL) and washed with saturated aqueous sodium hydrogencarbonate solution (100 mL). The aqueous phase was back extracted once with ethyl acetate (100 mL) and the combined organic phases were dried over sodium sulfate. Chromatography on silica gel with dichloromethane/methanol (12:1) gave 2.0 g (76%), mp 73° C.

후처리

  1. customThe solvent was removed under reduced pressure
  2. washwashed with saturated aqueous sodium hydrogencarbonate solution (100 mL)
  3. extractionThe aqueous phase was back extracted once with ethyl acetate (100 mL)
  4. dry with materialthe combined organic phases were dried over sodium sulfate
  5. customChromatography on silica gel with dichloromethane/methanol (12:1) gave 2.0 g (76%), mp 73° C.

출처 및 근거

ORD 기록
ord-b3ede395496f40239e525777266fb079
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08124602B2

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