Cyclohexanone → HCID 19040168, compound

HRID 232553Notes

Reaction equation

HRID 232553 reaction equation
[C:1]([CH:5]1[CH2:17][CH2:16][C:8]2([O:12][CH2:11][C:10]([CH2:14][NH2:15])([OH:13])[CH2:9]2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[C:18]1(=O)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.C([BH3-])#N.[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[C:1]([CH:5]1[CH2:17][CH2:16][C:8]2([O:12][CH2:11][C:10]([CH2:14][NH:15][CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)([OH:13])[CH2:9]2)[CH2:7][CH2:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 7967CyclohexanoneHCID 5003444Sodium cyanoborohydrideHCID 19040154HCID 19040154, compound

Product 1

HCID 19040168HCID 19040168, compoundYield 82.4%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 8-t-butyl-3-aminomethyl-3-hydroxy-1-oxaspiro-(4,5)decane (1.8 g, 7.5 mmol), cyclohexanone (1.36 g, 8 mmol) and zinc chloride (0.61 g, 4.5 mmol) in methanol (20 ml) was added sodium cyanoborohydride (0.56 g, 9 mmol). The reaction mixture was stirred at room temperature overnight. The solvent was then evaporated in vacuo and to the resulting residue was added saturated sodium carbonate solution and toluene (50 ml each). The organic layer was separated, dried (MgSO4) and evaporated in vacuo to yield a semisolid residue (2.0 g) which was treated with light petroleum. A colourless powder was isolated by filtration (1.0 g) which melted at 113°-115° C.

Workup

  1. customThe solvent was then evaporated in vacuo and to the resulting residue
  2. additionwas added saturated sodium carbonate solution and toluene (50 ml each)
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-081a3a8b04ca478bae2aa735cebfffe5
Source dataset
uspto-grants-1997_01
Patent number
US05591741

Reaction notes

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