HCID 86618162, compound → HCID 86618165, compound

HRID 2246606Notes

Reaction equation

HRID 2246606 reaction equation
C(OC([NH:11][C@H:12]1[CH2:17][CH2:16][C@@H:15]([O:18][CH3:19])[CH2:14][C@H:13]1[CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=O)C1C=CC=CC=1.[H][H]>CO.[Pd]>[NH2:11][C@H:12]1[CH2:17][CH2:16][C@@H:15]([O:18][CH3:19])[CH2:14][C@H:13]1[CH2:20][NH:21][C:22](=[O:28])[O:23][C:24]([CH3:26])([CH3:25])[CH3:27]

Participants

5

Reactant 2

HCID 86618162HCID 86618162, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 86618165HCID 86618165, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A sample of the product from Step 5 was dissolved in MeOH (100 ml). Palladium on carbon (0.185 g, 1.743 mmol) was added to the solution and the reaction mixture was stirred under 50 psi hydrogen for 2 h. The reaction mixture was filtered through Celite with EtOAc. The resulting solution was concentrated in vacuo to yield tert-butyl ((1S,2S,5R)-2-amino-5-methoxycyclohexyl)methylcarbamate as a clear oil which was used without any further purification. A quantitative yield was assumed. LC/MS found [M+H]+=259.41.

Workup

  1. filtrationThe reaction mixture was filtered through Celite with EtOAc
  2. concentrationThe resulting solution was concentrated in vacuo

Sources & evidence

ORD record
ord-118c88cb8e904f71b6259c3da5094932
Source dataset
uspto-grants-2010_03
Patent number
US07687508B2

Reaction notes

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