Sodium Hydroxide → (S)-2,2-Diphenyl-2-(pyrrolidin-3-yl)acetamide

HRID 1742705Notes

Reaction equation

HRID 1742705 reaction equation
C([C@@H]([C@H](C(O)=O)O)O)(O)=O.[C:11]([C:14]([C@@H:27]1[CH2:31][CH2:30][NH:29][CH2:28]1)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:13])[NH2:12].[OH-].[Na+]>O>[C:11]([C:14]([C@@H:27]1[CH2:31][CH2:30][NH:29][CH2:28]1)([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)(=[O:13])[NH2:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 24968963(2R,3R)-2,3-Dihydroxybutanedioic acid--2,2-diphenyl-2-[(3S)-pyrrolidin-3-yl]acetamide (1/1)2×

Product 1

HCID 13633758(S)-2,2-Diphenyl-2-(pyrrolidin-3-yl)acetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-(S)-(+)-(1-Carbamoyl-1,1-diphenylmethyl)pyrrolidine L-(+)-tartrate from part (A) (0.95 g) was dissolved in water (40 ml) and basified (pH 12) by the dropwise addition of 10% aqueous sodium hydroxide. The mixture was extracted with dichloromethane (2×50 ml), the extracts were combined, dried (Na2SO4), and concentrated in vacuo to give the title compound as a colourless foam, yield 0.64 g.

Workup

  1. extractionThe mixture was extracted with dichloromethane (2×50 ml)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dea218190ae748e0b45a088036f6d2af
Source dataset
uspto-grants-1994_08
Patent number
US05340831

Reaction notes

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