Oxygen → (3S,4S)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidine-3-carboxylic acid

HRID 1799776Notes

Reaction equation

HRID 1799776 reaction equation
O=O.[CH2:3]([N:10]1[CH2:14][C:13]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=2)=[C:12]([C:23]([OH:25])=[O:24])[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[H][H]>CO>[CH2:3]([N:10]1[CH2:14][C@H:13]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[C:17]([Cl:22])[CH:16]=2)[C@H:12]([C:23]([OH:25])=[O:24])[CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 977OxygenHCID 593718131-Benzyl-4-(3,4-dichloro-phenyl)-2,5-dihydro-1H-pyrrole-3-carboxylic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 46832836(3S,4S)-1-Benzyl-4-(3,4-dichloro-phenyl)-pyrrolidine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 185-ml stainless steel autoclave was charged under argon in a glove box (O2 content≦2 ppm) with 1-benzyl-4-(3,4-dichloro-phenyl)-2,5-dihydro-1H-pyrrole-3-carboxylic acid (1.00 g, 2.87 mmol), [Ru(OAc)2((R)-TMBTP)] (1.16 mg, 1.44×10−6 mol, S/C 2′,000) and methanol (30 ml). The asymmetric hydrogenation was run for 20 h at 30° C. under 40 bar of hydrogen (18.5% conversion). After the pressure was released, the off-white suspension was evaporated to dryness to yield 0.98 g (12%) of crude (S,S)-Ib with 12.1% purity and 94.5% ee.

Workup

  1. customthe off-white suspension was evaporated to dryness
  2. customto yield 0.98 g (12%) of crude (S,S)-Ib with 12.1% purity and 94.5% ee

Sources & evidence

ORD record
ord-0ec9c268ffdc4ea7abaed34a73267ee2
Source dataset
uspto-grants-2013_01
Patent number
US08344161B2

Reaction notes

Loading…