HCID 59468965, compound → HCID 59468953, compound

HRID 1690086Notes

Reaction equation

HRID 1690086 reaction equation
[NH2:1][C:2]([C@:4]1([CH3:30])[CH2:8][CH2:7][C@H:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15]CC3C=CC=CC=3)=[CH:11][CH:10]=2)[N:5]1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:3]>CO.[Pd]>[NH2:1][C:2]([C@:4]1([CH3:30])[CH2:8][CH2:7][C@H:6]([C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[N:5]1[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])=[O:3]

Participants

4

Reactant 1

HCID 59468965HCID 59468965, compound

Product 1

HCID 59468953HCID 59468953, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 1,1-dimethylethyl (2S,5R)-2-(aminocarbonyl)-2-methyl-5-{4-[(phenylmethyl)oxy]phenyl}-1-pyrrolidinecarboxylate (D9, 850 mg, 2.07 mmol) in methanol (10 ml) was added Pd/C 10% wt (85 mg, 10 wt %) and the mixture was stirred under hydrogen (1 atmosphere) for 5 hours. The catalyst was filtered off and the solvent removed under reduced pressure to give the title compound as a white solid (D10, 623 mg, 94%); Rt (HPLC): 4.00 min; 1H NMR (500 MHz, DMSO-d6) δ(ppm): 9.16 (s, 1H), 7.28-7.42 (m, 1H), 7.16-7.26 (m, 2H), 7.02-7.14 (m, 1H), 6.59-6.68 (m, 2H), 4.56-4.85 (m, 1H), 2.07-2.41 (m, 2H), 1.52-1.77 (m, 2H), 1.51 (s, 3H), 1.31 and 1.05 (s, s, 9 H).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-98446e45f4b249e1bbd024a0fe371fef
Source dataset
uspto-grants-2012_04
Patent number
US08153623B2

Reaction notes

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