1-Benzyl-4-(4-chloro-3-fluoro-phenyl)-2,5-dihydro-1H-pyrrole-3-carboxylic acid → (3S,4S)-1-Benzyl-4-(4-chloro-3-fluoro-phenyl)-pyrrolidine-3-carboxylic acid

HRID 1799779Notes

Reaction equation

HRID 1799779 reaction equation
[CH2:1]([N:8]1[CH2:12][C:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([F:20])[CH:14]=2)=[C:10]([C:21]([OH:23])=[O:22])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H][H]>CO>[CH2:1]([N:8]1[CH2:12][C@H:11]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[C:15]([F:20])[CH:14]=2)[C@H:10]([C:21]([OH:23])=[O:22])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 583126211-Benzyl-4-(4-chloro-3-fluoro-phenyl)-2,5-dihydro-1H-pyrrole-3-carboxylic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 46832839(3S,4S)-1-Benzyl-4-(4-chloro-3-fluoro-phenyl)-pyrrolidine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 2-l Hastelloy C4 autoclave was charged under argon with 1-benzyl-4-(4-chloro-3-fluoro-phenyl)-2,5-dihydro-1H-pyrrole-3-carboxylic acid (30.0 g, 90.4 mmol), [Ru(OAc)2((R)-2-Furyl-MeOBIPHEP)] (275.5 mg, 0.36 mmol, S/C 250) and methanol (1.2 l). The asymmetric hydrogenation was run for 20 h at 30° C. under 40 bar of hydrogen (99.2% conversion). After the pressure was released, a sample of the white suspension was evaporated to dryness. Crude (S,S)-Id was obtained with 97.9% purity and >99.9% ee.

Workup

  1. customa sample of the white suspension was evaporated to dryness
  2. customCrude (S,S)-Id was obtained with 97.9% purity and >99.9% ee

Sources & evidence

ORD record
ord-0b34f5183d41418aa1c616df9064acd1
Source dataset
uspto-grants-2013_01
Patent number
US08344161B2

Reaction notes

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