Sodium borohydride → 8-t-Butyl-3-hydroxy-1-oxaspiro(4,5)decane

HRID 232546Notes

Reaction equation

HRID 232546 reaction equation
[C:1]([CH:5]1[CH2:15][CH2:14][C:8]2([O:12][CH2:11][C:10](=[O:13])[CH2:9]2)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].[H][H]>CO>[C:1]([CH:5]1[CH2:15][CH2:14][C:8]2([O:12][CH2:11][CH:10]([OH:13])[CH2:9]2)[CH2:7][CH2:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 151828188-t-Butyl-1-oxaspiro(4,5)decane-3-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 190401578-t-Butyl-3-hydroxy-1-oxaspiro(4,5)decaneYield 98,679.102%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To an ice cooled solution of 8-t-butyl-1-oxaspiro(4,5)decane-3-one (44.1 g, 0.21 mmol) in methanol (300 ml) was added sodium borohydride (10.8 g, 0.285 mol) in portions. After the evolution of hydrogen ceased the cooling bath was removed and the mixture was stirred at room temperature over night. The solvent was evaporated in vacuo and the residue was taken up in toluene/diluted hydrochloric acid. The organic layer was washed twice with water (200 ml), dried (MgSO4) and evaporated in vacuo to yield a colourless oil (44 g) which was recrystallised from light petroleum. 30 g of colourless crystals were obtained which melted at 82°-84° C. TLC and NMR-analysis indicated a single diastereoisomer only (cis).

Workup

  1. customwas removed
  2. customThe solvent was evaporated in vacuo
  3. washThe organic layer was washed twice with water (200 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-95b7c425cf0146ccb9296b6db133875d
Source dataset
uspto-grants-1997_01
Patent number
US05591741

Reaction notes

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