Hydrochloric Acid → (S)-4-Hydroxy-1-[4-(1-pyrrolidinyl)2-butynyl]-2-pyrrolidinone

HRID 2107996Notes

Reaction equation

HRID 2107996 reaction equation
CC([Si](C)(C)[O:6][C@@H:7]1[CH2:11][N:10]([CH2:12][C:13]#[C:14][CH2:15][N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[C:9](=[O:21])[CH2:8]1)(C)C.Cl.[OH-].[K+]>>[OH:6][C@@H:7]1[CH2:11][N:10]([CH2:12][C:13]#[C:14][CH2:15][N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)[C:9](=[O:21])[CH2:8]1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 15086817(S)-4-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-1-[4-(1-pyrrolidinyl)-2-butynyl]-2-pyrrolidinone

Product 1

HCID 15046677(S)-4-Hydroxy-1-[4-(1-pyrrolidinyl)2-butynyl]-2-pyrrolidinoneYield 8.4%

Procedure

A mixture of 7.2 g of (S)-4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-[4-(1-pyrrolidinyl)-2-butynyl]-2-pyrrolidinone and 75 ml of 1N methanolic hydrochloric acid was stirred for 1 hour, then cooled to 0° C. and basified to pH 8 with methanolic potassium hydroxide. The mixture was filtered and the filtrate evaporated. The residue was reevaporated from dichloromethane. The residual oil was purified by chromatography (alumina), giving 0.4 g of the desired product as a yellow oil, [α]D26 =-12° (dichloromethane).

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate evaporated
  3. customThe residue was reevaporated from dichloromethane
  4. customThe residual oil was purified by chromatography (alumina)

Sources & evidence

ORD record
ord-fe0c09993bc44245a17e751a6bf07485
Source dataset
uspto-grants-1990_06
Patent number
US04937235

Reaction notes

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