Sodium borohydride → HCID 14521578, compound

HRID 276122Notes

Reaction equation

HRID 276122 reaction equation
[BH4-].[Na+].[C:3]([CH:7]1[C:13](=[O:14])[CH2:12][CH:11]2[O:15][CH:8]1[CH2:9][CH2:10]2)([O:5][CH3:6])=[O:4]>CO>[C:3]([CH:7]1[CH:13]([OH:14])[CH2:12][CH:11]2[O:15][CH:8]1[CH2:9][CH2:10]2)([O:5][CH3:6])=[O:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 14521576HCID 14521576, compound

Product 1

HCID 14521578HCID 14521578, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

NaBH4 (2.56 g, 67.7 mmol) was added to a solution of 2-carbomethoxy-8-oxabicyclo(3.2.1)octan-3-one, 3, (5.12 g, 27.8 mmol) in MeOH (100 mL) at −78° C. The reaction mixture was left at room temperature overnight. The solution was concentrated to dryness. The residue was dissolved in water (50 mL), and extracted with CH2Cl2 (100, 2×50 mL). The combined dried (MgSO4) extracts were concentrated to dryness (yield: 3.9 g). By repeated flash column chromatography four isomers were obtained from the residue (2.9 g). The major isomer was 2α-carbomethoxy-3α-hydroxy-8-oxabicyclo(3.2.1)octane (1.0 g, 26%). Some of the other isomers were isolated to be used in the following reactions but there were still mixed fractions. Other pure isomers obtained:

Workup

  1. concentrationThe solution was concentrated to dryness
  2. dissolutionThe residue was dissolved in water (50 mL)
  3. extractionextracted with CH2Cl2 (100, 2×50 mL)
  4. dry with materialThe combined dried (MgSO4) extracts
  5. concentrationwere concentrated to dryness (yield: 3.9 g)

Sources & evidence

ORD record
ord-54ca0f56b5604d82b731429d4a85286e
Source dataset
uspto-grants-2002_03
Patent number
US06353105B1

Reaction notes

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