Methanol → Acetamide, N-methyl-N-[4-(3-hydroxypyrrolidinyl)-2-butynyl]-

HRID 1710136Notes

Reaction equation

HRID 1710136 reaction equation
C([O:4][CH:5]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]#[C:12][CH2:13][N:14]([CH3:18])[C:15](=[O:17])[CH3:16])[CH2:6]1)(=O)C.C(=O)([O-])[O-].[Na+].[Na+].CO>ClCCl>[OH:4][CH:5]1[CH2:9][CH2:8][N:7]([CH2:10][C:11]#[C:12][CH2:13][N:14]([CH3:18])[C:15](=[O:17])[CH3:16])[CH2:6]1

Participants

5

Reactant 3

HCID 887MethanolHCID 10340Sodium CarbonateHCID 15086787(Racemic)-N-[4-[3-(Acetyloxy)-1-pyrrolidinyl]-2-butynyl]-N-methyl acetamide

Product 1

HCID 536669Acetamide, N-methyl-N-[4-(3-hydroxypyrrolidinyl)-2-butynyl]-Yield 73.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 820 mg of (racemic)-N-[4-[3-(acetyloxy)-1-pyrrolidinyl]-2-butynyl]-N-methyl acetamide, 635 mg of sodium carbonate and 40 ml of methanol was stirred overnight. An equal volume of dichloromethane was added, the mixture filtered and the solvents concentrated. This residue was purified by chromatography (alumina), giving 500 mg of the desired product as a yellow oil.

Workup

  1. filtrationthe mixture filtered
  2. concentrationthe solvents concentrated
  3. customThis residue was purified by chromatography (alumina)

Sources & evidence

ORD record
ord-e5b8326aa2434b0a833da132c5299aea
Source dataset
uspto-grants-1990_08
Patent number
US04952600

Reaction notes

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