2-Bromoethanol → (R)-2-(2-methylpyrrolidin-1-yl)ethanol

HRID 1522854ノート

反応式

HRID 1522854 の反応式
Cl.[CH3:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][NH:4]1.Br[CH2:9][CH2:10][OH:11].C([O-])([O-])=O.[K+].[K+]>C(#N)C>[CH3:2][C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[CH2:9][CH2:10][OH:11]

参加物

5

反応物 3

HCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 11147704(2R)-(-)-2-Methylpyrrolidine hydrochloride

生成物 1

HCID 45087381(R)-2-(2-methylpyrrolidin-1-yl)ethanol収率 24,020.5%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture of (R)-2-methylpyrrolidine hydrochloride (4 g, 0.03 mol), 2-bromoethanol (3.7 g, 0.029 mmol) and K2CO3 (8.28 g, 0.0618 mol) in acetonitrile (50 mL) was stirred at room temperature overnight. The mixture was filtered, and the filter cake was washed with ethyl acetate (100 mL). The combined filtrate was concentrated and the residue was purified on a silica gel column (MeOH/DCM=1/50) to give (R)-2-(2-methylpyrrolidin-1-yl)ethanol (0.9 g) as a colorless oil. 1H NMR (CDCl3): δ 3.63 (m, 2H), 3.14 (m, 1H), 2.95 (m, 1H), 2.44 (m, 1H), 2.24 (dt, 1H), 2.14 (m, 1H), 1.95 (m, 1H), 1.68 (m, 2H), 1.38 (m, 1H), 1.07 (d, 3H); LCMS: 130 (M+H)+.

後処理

  1. filtrationThe mixture was filtered
  2. washthe filter cake was washed with ethyl acetate (100 mL)
  3. concentrationThe combined filtrate was concentrated
  4. customthe residue was purified on a silica gel column (MeOH/DCM=1/50)

出典と根拠

ORDレコード
ord-ef3f4a0e23b040a5b343cdbe79b2daa7
出典データセット
uspto-grants-2015_07
特許番号
US09078871B2

反応ノート

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