HCID 178418361, compound → HCID 178455364, compound

HRID 2235231Notes

Reaction equation

HRID 2235231 reaction equation
C(OC(=O)[NH:10][C@H:11]1[CH2:16][CH2:15][C@H:14]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH2:13][CH2:12]1)C1C=CC=CC=1.[H][H]>CCOC(C)=O.[Pd]>[C:21]([Si:18]([CH3:20])([CH3:19])[O:17][C@H:14]1[CH2:13][CH2:12][C@H:11]([NH2:10])[CH2:16][CH2:15]1)([CH3:24])([CH3:23])[CH3:22]

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178455368HCID 178455368, compound

Product 1

HCID 178455364HCID 178455364, compoundYield 104.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Combine trans-[4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-carbamic acid benzyl ester (23.0 g, 0.06 mol), palladium, 10% wt. on activated carbon (0.5 g), in EtOAc (100 mL) and charge the flask with hydrogen (50 psi). After 3 hours, filter the reaction mixture through a pad of Celite® and evaporate the solvent to obtain trans-4-(tert-butyl-dimethyl-silanyloxy)-cyclohexylamine as a dark oil (14.4 g, 99%): MS (EI) m/z=229 (M+).

Workup

  1. filtrationfilter the reaction mixture through a pad of Celite®
  2. customevaporate the solvent

Sources & evidence

ORD record
ord-a22f3dcb6fb1409890aa376beeec5965
Source dataset
uspto-grants-2010_05
Patent number
US07713979B2

Reaction notes

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