HCID 178457353, compound → HCID 178457352, compound

HRID 2225218Notes

Reaction equation

HRID 2225218 reaction equation
C(OC(=O)[NH:10][CH2:11][C:12](=[O:25])[NH:13][C@H:14]1[CH2:19][CH2:18][C@@H:17]([N:20]([CH:22]([CH3:24])[CH3:23])[CH3:21])[CH2:16][CH2:15]1)C1C=CC=CC=1>[OH-].[OH-].[Pd+2].CO>[NH2:10][CH2:11][C:12]([NH:13][C@H:14]1[CH2:19][CH2:18][C@@H:17]([N:20]([CH:22]([CH3:24])[CH3:23])[CH3:21])[CH2:16][CH2:15]1)=[O:25]

Participants

4

Reactant 1

HCID 178457353HCID 178457353, compound

Product 1

HCID 178457352HCID 178457352, compoundYield 74.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

Example 1 h, Step 4: cis-{[4-(Isopropyl-methyl-amino)-cyclohexylcarbamoyl]-methyl}-carbamic acid benzyl ester (1.86 g), methanol (20 mL), and 20% Pd(OH)2 (400 mg) were hydrogenated until completion by TLC on a Parr shaker at 50 psi. Filtration through fiberglass filter paper under nitrogen and removal of solvent in vacuo yielded 870 mg of cis-2-amino-N-[4-(isopropyl-methyl-amino)-cyclohexyl]-acetamide. MS found: (M+H)+=227.

Workup

  1. customExample 1 h, Step 4
  2. filtrationFiltration through fiberglass
  3. filtrationfilter paper under nitrogen
  4. customremoval of solvent in vacuo

Sources & evidence

ORD record
ord-64c97144e2ca4cb59f7d71d64be8e534
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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