(R)-3-Oxiranylpyrrolidine-1-carboxylic acid t-butyl ester → (R)-(S)-3-Oxiranylpyrrolidine-1-carboxylic acid t-butyl ester

HRID 1026177Notes

Reaction equation

HRID 1026177 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([CH:13]2[CH2:15][O:14]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>O>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][C@@H:10]([C@H:13]2[CH2:15][O:14]2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 86664072(R)-3-Oxiranylpyrrolidine-1-carboxylic acid t-butyl ester

Product 1

HCID 86664073(R)-(S)-3-Oxiranylpyrrolidine-1-carboxylic acid t-butyl ester

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(R)-3-Oxiranylpyrrolidine-1-carboxylic acid t-butyl ester (30 g, 140.6 mmol, 1.0 eq.) was combined with (S,S)-Salen Co(II) (418 mg, 0.7 mmol). Water (⅓ mL) was added and the resulting mixture was stirred vigorously for 6 hours. Hexanes (200 mL) was added. The resulting solids were crushed and stirred in hexanes to yield a yellow precipitate. The precipitate was purified by column chromatography (200-300 mesh, hexanes:EtOAc=1:3, 3 L) to yield (R)—(S)-3-Oxiranylpyrrolidine-1-carboxylic acid t-butyl ester.

Workup

  1. customThe resulting solids were crushed
  2. customto yield a yellow precipitate
  3. customThe precipitate was purified by column chromatography (200-300 mesh, hexanes:EtOAc=1:3, 3 L)

Sources & evidence

ORD record
ord-c8afa39a0247412aae17fb0e43c70420
Source dataset
uspto-grants-2014_05
Patent number
US08729119B2

Reaction notes

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