benzyl 4-((1R,2S)-2-{2-[4-(2-azetidin-1-yl-2-oxoethyl)-3-fluorophenoxy]ethyl}cyclopropyl)piperidine-1-carboxylate → 4-((1R,2S)-2-{2-[4-(2-azetidin-1-yl-2-oxoethyl)-3-fluorophenoxy]ethyl)cyclopropyl)piperidine

HRID 1850763Notes

Reaction equation

HRID 1850763 reaction equation
[N:1]1([C:5](=[O:36])[CH2:6][C:7]2[CH:34]=[CH:33][C:10]([O:11][CH2:12][CH2:13][C@@H:14]3[CH2:16][C@@H:15]3[CH:17]3[CH2:22][CH2:21][N:20](C(OCC4C=CC=CC=4)=O)[CH2:19][CH2:18]3)=[CH:9][C:8]=2[F:35])[CH2:4][CH2:3][CH2:2]1>CO.[Pd]>[N:1]1([C:5](=[O:36])[CH2:6][C:7]2[CH:34]=[CH:33][C:10]([O:11][CH2:12][CH2:13][C@@H:14]3[CH2:16][C@@H:15]3[CH:17]3[CH2:18][CH2:19][NH:20][CH2:21][CH2:22]3)=[CH:9][C:8]=2[F:35])[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 70856384benzyl 4-((1R,2S)-2-{2-[4-(2-azetidin-1-yl-2-oxoethyl)-3-fluorophenoxy]ethyl}cyclopropyl)piperidine-1-carboxylate

Product 1

HCID 708563224-((1R,2S)-2-{2-[4-(2-azetidin-1-yl-2-oxoethyl)-3-fluorophenoxy]ethyl)cyclopropyl)piperidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of benzyl 4-((1R,2S)-2-{2-[4-(2-azetidin-1-yl-2-oxoethyl)-3-fluorophenoxy]ethyl}cyclopropyl)piperidine-1-carboxylate (590 mg, 1.32 mmol) in 8 mL anhydrous methanol at ambient temperature was added palladium on carbon (80.0 mg, 0.676 mmol), 10% by weight. The solution was stirred under hydrogen for 4 hours and filtered. The crude product was concentrated to the title compound as white solid and used for the next step. LC/MS 361.3 (M+H)+.

Workup

  1. filtrationfiltered
  2. concentrationThe crude product was concentrated to the title compound as white solid

Sources & evidence

ORD record
ord-497cbb93515a41bcaf5691d23df2d035
Source dataset
uspto-grants-2015_02
Patent number
US08957062B2

Reaction notes

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