Sodium triacetoxyborohydride → HCID 18338590, compound

HRID 2298499Notes

Reaction equation

HRID 2298499 reaction equation
[C:1]([O:5][C:6]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:13](=[O:18])[C:14]([O:16][CH3:17])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:1]([O:5][C:6]([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH:13]([OH:18])[C:14]([O:16][CH3:17])=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 5049666Sodium triacetoxyborohydrideHCID 18338592HCID 18338592, compound

Product 1

HCID 18338590HCID 18338590, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of crude methyl 7-tert-butoxycarbonyl-2-oxoheptanoate (1 g) in 1,2-dichloroethane (10 ml) was treated with sodium triacetoxyborohydride (822 mg, 3.88 mmol). The mixture was stirred at room temperature for 16 hours, quenched with sat. aq. sodium bicarbonate and extracted with ether. The organic phase was washed with aq. sodium bicarbonate, brine, dried over sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel (hexane:ethyl acetate=4:1) to give the title compound (554 mg, 43%, 2 steps) as a colorless liquid.

Workup

  1. customquenched with sat. aq. sodium bicarbonate
  2. extractionextracted with ether
  3. washThe organic phase was washed with aq. sodium bicarbonate, brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was chromatographed on silica gel (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-6d2ba1ca042c4ac4b6a870476f39e4e9
Source dataset
uspto-grants-2002_12
Patent number
US06492550B2

Reaction notes

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