Acetone → HCID 178457354, compound

HRID 2225215Notes

Reaction equation

HRID 2225215 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C@H:8]1[CH2:13][CH2:12][C@@H:11]([NH2:14])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[CH3:16][C:17]([CH3:19])=O.[BH3-][C:21]#N.[Na+].C=O>CO>[C:1]([O:5][C:6](=[O:15])[NH:7][C@H:8]1[CH2:9][CH2:10][C@@H:11]([N:14]([CH:17]([CH3:19])[CH3:16])[CH3:21])[CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 180AcetoneHCID 712FormaldehydeHCID 5003444Sodium cyanoborohydrideHCID 178418966HCID 178418966, compound

Product 1

HCID 178457354HCID 178457354, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (cis-4-amino-cyclohexyl)-carbamic acid tert-butyl ester (1.8 g, 8.3 mmol) in MeOH (20 mL) was charged with acetone (2 mL), stirred for 10 minutes, charged with NaCNBH3 (1.6 g, 24.9 mmol), stirred for 3 h, charged with formaldehyde (1 mL of a 37% aq. Solution), stirred for 1.5 h, and then concentrated in vacuo. The residue was dissolved in EtOAc and the solution was washed successively with water and brine before being dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified via flash chromatography to afford [cis-4-(isopropyl-methyl-amino)-cyclohexyl]-carbamic acid tert-butyl ester (1.4 g, 62% yield). MS found: (M+H)+=271.3.

Workup

  1. stirringstirred for 3 h
  2. stirringstirred for 1.5 h
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in EtOAc
  5. washthe solution was washed successively with water and brine
  6. dry with materialbefore being dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified via flash chromatography

Sources & evidence

ORD record
ord-99003a905da94708a30547356050e092
Source dataset
uspto-grants-2008_05
Patent number
US07378409B2

Reaction notes

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