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

HRID 1644312ノート

反応式

HRID 1644312 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
70 °C

実験手順

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.

後処理

  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.

出典と根拠

ORDレコード
ord-b3ede395496f40239e525777266fb079
出典データセット
uspto-grants-2012_02
特許番号
US08124602B2

反応ノート

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