Sodium borohydride → tert-Butyl 2-hydroxy-6-azaspiro(3.4)octane-6-carboxylate

HRID 1943593Notes

Reaction equation

HRID 1943593 reaction equation
[BH4-].[Na+].[O:3]=[C:4]1[CH2:7][C:6]2([CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8]2)[CH2:5]1>CO>[OH:3][CH:4]1[CH2:5][C:6]2([CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8]2)[CH2:7]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 23565399tert-Butyl 2-oxo-6-azaspiro[3.4]octane-6-carboxylate

Product 1

HCID 69669842tert-Butyl 2-hydroxy-6-azaspiro(3.4)octane-6-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.89 g (23.57 mmoles) of sodium borohydride is added in portions at 0° C. to a solution of 3.54 g (15.71 mmoles) of tert-butyl 2-oxo-6-aza-spiro[3.4]octane-6-carboxylate (WO 9806720) diluted in 40 ml of methanol. The reaction mixture is stirred for 1 hr and 30 mins at ambient temperature. After evaporation of the solvent, water is added to the reaction mixture, the aqueous phase is separated, it is extracted several times with diethyl ether, and the combined organic phases are washed with a saturated aqueous solution of sodium chloride, they are dried over sodium sulphate and the filtrate is concentrated under reduced pressure. After evaporation of the solvent, 3.10 g of product are obtained in the form of a brown oil used as such in the following stage.

Workup

  1. customAfter evaporation of the solvent, water
  2. additionis added to the reaction mixture
  3. customthe aqueous phase is separated
  4. extractionit is extracted several times with diethyl ether
  5. washthe combined organic phases are washed with a saturated aqueous solution of sodium chloride, they
  6. dry with materialare dried over sodium sulphate
  7. concentrationthe filtrate is concentrated under reduced pressure
  8. customAfter evaporation of the solvent, 3.10 g of product
  9. customare obtained in the form of a brown oil

Sources & evidence

ORD record
ord-88576e71fd4442368b89b695746eca49
Source dataset
uspto-grants-2013_03
Patent number
US08394787B2

Reaction notes

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