Sodium borohydride → 3-Hydroxy-2,8-dimethyl-1-oxa-8-azaspiro[4.5]decane

HRID 1728244Notes

Reaction equation

HRID 1728244 reaction equation
[CH3:1][CH:2]1[C:6](=[O:7])[CH2:5][C:4]2([CH2:12][CH2:11][N:10]([CH3:13])[CH2:9][CH2:8]2)[O:3]1.[BH4-].[Na+]>C(O)C>[NH3:10].[OH:7][CH:6]1[CH2:5][C:4]2([CH2:12][CH2:11][N:10]([CH3:13])[CH2:9][CH2:8]2)[O:3][CH:2]1[CH3:1]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 101764012,8-Dimethyl-1-oxa-8-azaspiro[4.5]decan-3-one

Product 2

HCID 222AmmoniaHCID 103975203-Hydroxy-2,8-dimethyl-1-oxa-8-azaspiro[4.5]decaneYield 197.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2,8-dimethyl-1-oxa-8-azaspiro[4.5]-decan-3-one (200 mg) in 7 ml ethanol, was added 25 mg sodium borohydride at room temperature, and the mixture was stirred at room temperature for two hours. The reaction mixture was cooled in an ice-water bath, acidified by addition of 6N--HCL (to about pH 4), and stirred for about 20 minutes with the ice-water bath removed. Ethanol was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography by using, as eluent, a mixed solvent of chloroform/methanol/conc. ammonia (5:1:0.1 by volume), giving 200 mg of 3-hydroxy-2,8-dimethyl-1-oxa-8-azaspiro[4.5]decane as oil. It was dissolved in ether, and ehtanolic hydrogen chloride was added to this solution, thus giving its hydrochloride as white crystals.

Workup

  1. temperatureThe reaction mixture was cooled in an ice-water bath
  2. additionacidified by addition of 6N
  3. customremoved
  4. distillationEthanol was distilled off under reduced pressure
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1ff82e21822c4e92af16c3699307a425
Source dataset
uspto-grants-1994_07
Patent number
USRE034653

Reaction notes

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