HCID 59468967, compound → HCID 59468926, compound

HRID 1690118Notes

Reaction equation

HRID 1690118 reaction equation
[NH2:1][C:2]([C@:4]1([CH2:34][O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37])[CH2:8][CH2:7][C@H:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[F:23])=[CH:11][CH:10]=2)[N:5]1C(OCC1C=CC=CC=1)=O)=[O:3]>CO.[Pd]>[CH3:42][C:39]([Si:36]([CH3:38])([CH3:37])[O:35][CH2:34][C@@:4]1([C:2]([NH2:1])=[O:3])[CH2:8][CH2:7][C@H:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[F:23])=[CH:11][CH:10]=2)[NH:5]1)([CH3:40])[CH3:41]

Participants

4

Reactant 1

HCID 59468967HCID 59468967, compound

Product 1

HCID 59468926HCID 59468926, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of phenylmethyl (2R,5R)-2-(aminocarbonyl)-2-({[(1,1-dimethylethyl)(dimethyl)silyl]oxy}methyl)-5-(4-{[(2-fluorophenyl)methyl]oxy}phenyl)-1-pyrrolidinecarboxylate (D74, 85 mg, 0.14 mmol) in methanol (2 ml) was added palladium (10 mg, 10 wt. % dry basis on activated carbon) and the mixture was stirred under hydrogen atmosphere (1 atm) for 30 min. The catalyst was filtered off, the solvent removed under reduced pressure and the crude material purified by chromatography on silica gel using cyclohexane and ethyl acetate (9:1 to 75:25) to afford the title compound (50 mg, 79%) as a colourless oil; Rt (HPLC): 5.00 min; MS: (ES/+) m/z: 459 [MH]+ C25H35FN2O3Si requires 458.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe solvent removed under reduced pressure
  3. customthe crude material purified by chromatography on silica gel

Sources & evidence

ORD record
ord-edb5a5f263c148938cb9189f4637d67d
Source dataset
uspto-grants-2012_04
Patent number
US08153623B2

Reaction notes

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