Oxygen → (3R,4R)-1-Benzyl-4-(4-chloro-3-fluoro-phenyl)-pyrrolidine-3-carboxylic acid

HRID 527496Notes

Reaction equation

HRID 527496 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]([F: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.COC1C(C2C(OC)=CC=CC=2P(C2OC=CC=2)C2OC=CC=2)=C(P(C2OC=CC=2)C2OC=CC=2)C=CC=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]([F: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

6

Reactant 4

HCID 977OxygenHCID 15307805(S)-(-)-2,2'-Bis(di-2-furanylphosphino)-6,6'-dimethoxy-1,1'-biphenylHCID 583126211-Benzyl-4-(4-chloro-3-fluoro-phenyl)-2,5-dihydro-1H-pyrrole-3-carboxylic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 46833134(3R,4R)-1-Benzyl-4-(4-chloro-3-fluoro-phenyl)-pyrrolidine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

An autoclave was charged under argon in a glove box (O2 content<2 ppm) with 1-Benzyl-4-(4-chloro-3-fluoro-phenyl)-2,5-dihydro-1H-pyrrole-3-carboxylic acid (1.00 g, 3.01 mmol), [Ru(OAc)2((S)-2-furyl-MeOBIPHEP)] (9.18 mg, 0.012 mmol) (2-furyl-MeOBIPHEP=(6,6′-dimethoxybiphenyl-2,2′-diyl)bis(di-2-furylphosphine) and methanol (30 mL). The asymmetric hydrogenation was run for 20 h at 30° C. under 40 bar of hydrogen. After the pressure was released, the grey suspension was evaporated to dryness to yield the crude title compound. MS m/e: 332.1 [M−H].

Workup

  1. customthe grey suspension was evaporated to dryness

Sources & evidence

ORD record
ord-c9efb7e4010c440c9c89772e32f33615
Source dataset
uspto-grants-2016_05
Patent number
US09346786B2

Reaction notes

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