Sodium borohydride → HCID 66978202, compound

HRID 1807337Notes

Reaction equation

HRID 1807337 reaction equation
[CH3:1][C:2]12[CH2:9][CH:6]([CH2:7][CH2:8]1)[CH:5]([CH3:10])[C:4](=[O:11])[CH2:3]2.[BH4-].[Na+]>C(O)(C)C>[CH3:1][C:2]12[CH2:9][CH:6]([CH2:7][CH2:8]1)[CH:5]([CH3:10])[CH:4]([OH:11])[CH2:3]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 66974043HCID 66974043, compound

Product 1

HCID 66978202HCID 66978202, compoundYield 95.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

1,4-Dimethyl-bicyclo[3.2.1]octan-3-one (160 g, 1.05 mol, obtained as above in EXAMPLE III) was added to a NaBH4 suspension (12 g, 0.33 mol) in isopropanol (200 mL), and refluxed for 30 minutes. The reaction mixture was cooled to room temperature, and quenched with acetone followed by acetic acid. The organic layer was separated and concentrated to provide crude 1,4-dimethyl-bicyclo[3.2.1]octan-3-ol (150 g, 1.0 mol), which was then added to dimethyl carbonate (CO(OCH3)2, 270 g, 3 mol), and potassium tert-butoxide ((CH3)3COK, 25 g), and refluxed for 3 hours. The volatile ingredients were removed with a Dean Stark trap. The reaction mixture was subsequently quenched with acetic acid, and washed with water. Fractional distillation of the organic layer provided carbonic acid 1,4-dimethyl-bicyclo[3.2.1]oct-3-yl ester methyl ester (125 g) having a boiling point of 65° C. at a pressure of 0.5 mmHg

Workup

  1. temperaturerefluxed for 30 minutes
  2. customquenched with acetone
  3. customThe organic layer was separated
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-12872f2c8da6436682848b9f891bf1af
Source dataset
uspto-grants-2013_01
Patent number
US08357357B2

Reaction notes

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