Methanol → (R)-3-Hydroxy-1-[4-(1-pyrrolidinyl)-2-butynyl]-2-pyrrolidinone

HRID 2107976Notes

Reaction equation

HRID 2107976 reaction equation
[N+](C1C=CC(C([O:10][C@@H:11]2[CH2:15][CH2:14][N:13]([CH2:16][C:17]#[C:18][CH2:19][N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)[C:12]2=[O:25])=O)=CC=1)([O-])=O.C(=O)([O-])[O-].[K+].[K+].CO>ClCCl>[OH:10][C@@H:11]1[CH2:15][CH2:14][N:13]([CH2:16][C:17]#[C:18][CH2:19][N:20]2[CH2:21][CH2:22][CH2:23][CH2:24]2)[C:12]1=[O:25]

Participants

5

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 15086779(R)-3-[(4-Nitrobenzoyl)oxy]-1-[4-(1-pyrrolidinyl)-2-butynyl]-2-pyrrolidinone

Product 1

HCID 15046676(R)-3-Hydroxy-1-[4-(1-pyrrolidinyl)-2-butynyl]-2-pyrrolidinoneYield 83.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1.6 g of (R)-3-[(4-Nitrobenzoyl)-oxy]-1-[4-(1-pyrrolidinyl)-2-butynyl]-2-pyrrolidinone, 1.6 g of potassium carbonate and 60 ml of methanol was stirred for 2 hours, diluted with dichloromethane and filtered. The filtrate was concentrated to dryness. The residue was chromatographed (alumina) to give 0.8 g of the desired product as an off white solid; mp 81°-85° C.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated to dryness
  3. customThe residue was chromatographed (alumina)

Sources & evidence

ORD record
ord-43c78dfd3d584137be9a6fa2b40a91d3
Source dataset
uspto-grants-1990_06
Patent number
US04937235

Reaction notes

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