Cyclohexanone → 8-t-Butyl-3-cyclohexylaminomethyl-1-oxaspiro-(4,5)decane

HRID 232550Notes

Reaction equation

HRID 232550 reaction equation
[C:1]([CH:5]1[CH2:16][CH2:15][C:8]2([O:12][CH2:11][CH:10]([CH2:13][NH2:14])[CH2:9]2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[C:17]1(=O)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1.C([BH3-])#N.[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[C:1]([CH:5]1[CH2:16][CH2:15][C:8]2([O:12][CH2:11][CH:10]([CH2:13][NH:14][CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]3)[CH2:9]2)[CH2:7][CH2:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 7967CyclohexanoneHCID 5003444Sodium cyanoborohydrideHCID 190401518-t-Butyl-3-aminomethyl-1-oxaspiro(4,5)decane

Product 1

HCID 190401538-t-Butyl-3-cyclohexylaminomethyl-1-oxaspiro-(4,5)decaneYield 104.3%

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 8-t-butyl-3-aminomethyl-1-oxaspiro(4,5)-decane (1.2 g, 5.3 mmol), cyclohexanone (0.54 g, 5.5 mmol) and zinc chloride (0.4 g, 3 mmol) in methanol (15 ml) was added sodium cyanoborohydride (0.4 g, 6.4 mmol). The reaction mixture was stirred over night. The solvent was then evaporated in vacuo and the resulting residue was treated with a mixture of saturated aqueous sodium carbonate/toluene (50 ml each). The organic layer was separated, dried (MgSO4) and evaporated in vacuo to yield 1.7 g of a pale yellow oil which was purified by flash chromatography (toluene/ethanol 4:1). Evaporation of the fractions containing the product yielded a colourless oil (1.5 g).

Workup

  1. customThe solvent was then evaporated in vacuo
  2. additionthe resulting residue was treated with a mixture of saturated aqueous sodium carbonate/toluene (50 ml each)
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-c01db7beb72d4e20b86237a5c0429bb0
Source dataset
uspto-grants-1997_01
Patent number
US05591741

Reaction notes

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