Potassium Fluoride → Phenylmethyl (3S)-3-fluoro-1-pyrrolidinecarboxylate

HRID 1109730Notes

Reaction equation

HRID 1109730 reaction equation
[F-:1].[K+].[CH2:3]([O:10][C:11]([N:13]1[CH2:17][CH2:16][C@@H:15](O)[CH2:14]1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(O)CO>[CH2:3]([O:10][C:11]([N:13]1[CH2:17][CH2:16][C@H:15]([F:1])[CH2:14]1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 522689Potassium FluorideHCID 11183628(R)-(-)-1-CBZ-3-pyrrolidinol

Product 1

HCID 15197579Phenylmethyl (3S)-3-fluoro-1-pyrrolidinecarboxylate

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

A stirred mixture of 20.85 g (0.360 moles) of potassium fluoride spray-dried and 18.0 g (0.048 moles) of (3R)-N- benzyloxycarbonyl-3-hydroxypyrrolidine in 160 ml of freshly distilled ethylene glycol was kept at 85° C. for 15 h under nitrogen atmosphere.

Workup

  1. customspray-dried

Sources & evidence

ORD record
ord-b6e13fdfdacb4d11a3f0b479fc059b0f
Source dataset
uspto-grants-1994_06
Patent number
US05322848

Reaction notes

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