Methyl (2S)-5-(4-{[(2-fluorophenyl)methyl]amino}phenyl)-3,4-dihydro-2H-pyrrole-2-carboxylate → Methyl (5R)-5-(4-{[(2-fluorophenyl)methyl]amino}phenyl)-L-prolinate

HRID 2264818Notes

Reaction equation

HRID 2264818 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][NH:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH2:17][CH2:18][C@@H:19]([C:21]([O:23][CH3:24])=[O:22])[N:20]=2)=[CH:12][CH:11]=1.[H][H]>C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][NH:9][C:10]1[CH:15]=[CH:14][C:13]([C@@H:16]2[NH:20][C@H:19]([C:21]([O:23][CH3:24])=[O:22])[CH2:18][CH2:17]2)=[CH:12][CH:11]=1

Participants

4

Reactant 2

HCID 59596710Methyl (2S)-5-(4-{[(2-fluorophenyl)methyl]amino}phenyl)-3,4-dihydro-2H-pyrrole-2-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 59596688Methyl (5R)-5-(4-{[(2-fluorophenyl)methyl]amino}phenyl)-L-prolinateYield 92.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl (2S)-5-(4-{[(2-fluorophenyl)methyl]amino}phenyl)-3,4-dihydro-2H-pyrrole-2-carboxylate (D67, 39 mg, 0.119 mmol) and Pt 5% on carbon in ethyl acetate (10 ml) was stirred under 1 atm of hydrogen for 4.5 h, filtrated over celite and evaporated to afford the title compound (36 mg, 92%). MS: (ES/+) m/z: 329 [MH]+, —C19H21FN2O2 requires 328.

Workup

  1. filtrationfiltrated over celite
  2. customevaporated

Sources & evidence

ORD record
ord-32fd0f19fee4412985c864dd92392877
Source dataset
uspto-grants-2010_12
Patent number
US07855218B2

Reaction notes

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