HCID 178453647, compound → HCID 178453642, compound

HRID 1984874Notes

Reaction equation

HRID 1984874 reaction equation
C(OC(=O)[NH:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([CH2:17][NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:13][CH2:12]1)C1C=CC=CC=1>CO.CCCCCC.[Pd]>[C:22]([O:21][C:19](=[O:20])[NH:18][CH2:17][C@H:14]1[CH2:13][CH2:12][C@H:11]([NH2:10])[CH2:16][CH2:15]1)([CH3:25])([CH3:23])[CH3:24]

Participants

5

Reactant 1

HCID 178453647HCID 178453647, compound

Product 1

HCID 178453642HCID 178453642, compoundYield 100.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8058HexaneSolvent

Procedure

To a suspension of trans-[4-(tert-butoxycarbonylamino-methyl)-cyclohexyl]-carbamic acid benzyl ester (4.00 g, 11.0 mmol) in MeOH (40 mL) was added 5% Pd/C (400 mg). The mixture was stirred at ambient temperature under hydrogen atmosphere for 1 hr, filtered through a pad of celite, and concentrated to give a white solid. A suspension of the above solid in hexane (15 mL) was stirred at ambient temperature for 30 min. The solid was collected by filtration, washed with hexane, dried under reduced pressure to give trans-(4-amino-cyclohexylmethyl)-carbamic acid tert-butyl ester (2.52 g, 100%) as a white solid.

Workup

  1. filtrationfiltered through a pad of celite
  2. concentrationconcentrated
  3. customto give a white solid
  4. stirringwas stirred at ambient temperature for 30 min
  5. filtrationThe solid was collected by filtration
  6. washwashed with hexane
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-33d5f7d748f445be9e46a3eafd503093
Source dataset
uspto-grants-2009_06
Patent number
US07544690B2

Reaction notes

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