Water → Benzophenone O-[(R)-3-pyrrolidinyl]oxime

HRID 1182882Notes

Reaction equation

HRID 1182882 reaction equation
[OH-].[K+].[C:3](=[N:16][OH:17])([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.CS(O[C@H:23]1[CH2:27][CH2:26][N:25](OC(C)(C)C)[C:24]1=C=O)(=O)=O.O>CS(C)=O>[NH:25]1[CH2:26][CH2:27][C@@H:23]([O:17][N:16]=[C:3]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)[CH2:24]1

Participants

6

Reactant 4

HCID 962WaterHCID 11324Benzophenone oximeHCID 14797Potassium HydroxideHCID 86649201N-tert-butoxy-carbonyl-3-(S)-pyrrolidinyl methanesulfonate

Product 1

HCID 86635562Benzophenone O-[(R)-3-pyrrolidinyl]oxime

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a suspension of KOH powder (4.86 g) in DMSO (250 ml) under vigorous stirring, benzophenone oxime (7.86 g) was added. After stirring at RT for 30 min, a solution of N-tert-butoxy-carbonyl-3-(S)-pyrrolidinyl methanesulfonate (10.0 g) in DMSO (70 ml) was added. After 18 h at RT the reaction was poured into iced water (900 ml) and extracted with Et2O. The combined organic layers were washed with water, brine, dried and the solvent was evaporated. Benzophenone O-[(R)-3-pyrrolidinyl]oxime was obtained (13.0 g, 96%) as a white solid and used without any further purification in the next step.

Workup

  1. additionwas added
  2. extractionextracted with Et2O
  3. washThe combined organic layers were washed with water, brine
  4. customdried
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-f8f665f9d95d4dd090525fd18558d9b0
Source dataset
uspto-grants-2014_03
Patent number
US08664210B2

Reaction notes

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