Water → HCID 15086767, compound

HRID 2107972Notes

Reaction equation

HRID 2107972 reaction equation
[CH3:1][C:2](C)([O-])[CH3:3].[K+].[CH3:7][C:8]([Si:11]([CH3:20])([CH3:19])[O:12][C@H:13]1[CH2:17][CH2:16][NH:15][C:14]1=[O:18])([CH3:10])[CH3:9].C(Br)C#C.O>CN(C)C=O.C1(C)C=CC=CC=1>[CH3:10][C:8]([Si:11]([CH3:20])([CH3:19])[O:12][C@H:13]1[CH2:17][CH2:16][N:15]([CH2:3][C:2]#[CH:1])[C:14]1=[O:18])([CH3:7])[CH3:9]

Participants

7

Reactant 4

HCID 962WaterHCID 7842Propargyl bromideHCID 10584804(S)-3-((tert-Butyldimethylsilyl)oxy)pyrrolidin-2-oneHCID 23665647Potassium tert-butoxide

Product 1

HCID 15086767HCID 15086767, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
-20 °C

Procedure

A solution of 11.5 g of potassium tert-butoxide in 300 ml of dimethylformamide was cooled to -20° C. An 18 g portion of (S)-3-[[(1,1-dimethylethyl)dimethylsilyl]-oxy]-2-pyrrolidinone was added and the mixture stirred at -20° C. for 30 minutes. A 12 ml portion of 80% propargyl bromide in toluene was added and the reaction was allowed to warm to room temperature and was stirred for 1 hour. Water was added and the mixture was extracted with 5×100 ml of ether and 3×100 ml of dichloromethane. The extracts were combined, backwashed with water, dried and concentrated in vacuo, giving 15.8 g of (S)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-(2-propynyl)-2-pyrrolidinone [α]D260 =-44° (dichloromethane); mp 35°-36° C.

Workup

  1. temperatureto warm to room temperature
  2. stirringwas stirred for 1 hour
  3. extractionthe mixture was extracted with 5×100 ml of ether and 3×100 ml of dichloromethane
  4. customdried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-70d94e44cda74bf0ad60f06350ec7b76
Source dataset
uspto-grants-1990_06
Patent number
US04937235

Reaction notes

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