HCID 58291919, compound → HCID 58292070, compound

HRID 1944731Notes

Reaction equation

HRID 1944731 reaction equation
C([NH:8][CH:9]1[CH2:14][CH2:13][C:12]([NH:27][C:28](=[O:34])[O:29][C:30]([CH3:33])([CH3:32])[CH3:31])([C:15](=[O:26])[NH:16][C@@H:17]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)[CH3:18])[CH2:11][CH2:10]1)C1C=CC=CC=1.[H][H]>[Pd]>[C:30]([O:29][C:28](=[O:34])[NH:27][C:12]1([C:15](=[O:26])[NH:16][C@@H:17]([C:19]2[CH:20]=[CH:21][C:22]([F:25])=[CH:23][CH:24]=2)[CH3:18])[CH2:13][CH2:14][CH:9]([NH2:8])[CH2:10][CH2:11]1)([CH3:31])([CH3:32])[CH3:33]

Participants

4

Reactant 2

HCID 58291919HCID 58291919, compound2×HCID 178418361HCID 178418361, compound

Product 1

HCID 58292070HCID 58292070, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

(R)-tert-butyl 4-(benzylamino)-1-(1-(4-fluorophenyl)ethylcarbamoyl)cyclohexylcarbamate (Intermediate 94, the “cis” isomer, 87 mg) was hydrogenated at 1 atm hydrogen gas using 10% Pd/C (26 mg, Degussa type E101 NE/W 50% wet) for 16 hours. The reaction was filtered over celite to yield {4-Amino-1-[(R)-1-(4-fluoro-phenyl)-ethylcarbamoyl]-cyclohexyl}-carbamic acid tert-butyl ester (70 mg). MS MH+ 380.4

Workup

  1. customfor 16 hours
  2. filtrationThe reaction was filtered over celite

Sources & evidence

ORD record
ord-f61165cd24f0470785fd92c3687cf92c
Source dataset
uspto-grants-2013_03
Patent number
US08394858B2

Reaction notes

Loading…