Sodium triacetoxyborohydride → HCID 22166476, compound

HRID 2298506Notes

Reaction equation

[C:1]([O:5][C:6]([CH2:8][CH2:9][C:10](=[O:15])[C:11]([O:13][CH3:14])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(OC(CCCCCC(O)C(OC)=O)=O)(C)(C)C>>[C:1]([O:5][C:6]([CH2:8][CH2:9][CH:10]([OH:15])[C:11]([O:13][CH3:14])=[O:12])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

Reactant 3

HCID 5049666Sodium triacetoxyborohydride

HCID 18338590HCID 18338590, compound

HCID 22166479HCID 22166479, compound

Product 1

HCID 22166476HCID 22166476, compoundYield 28%

Procedure

Crude methyl 4-tert-butoxycarbonyl-2-oxobutanoate (1.65 g, 7.6 mmol) and sodium triacetoxyborohydride (1.6 g, 7.6 mmol) were reacted by the same procedure as described in Example 1 for the preparation of methyl 7-tert-butoxycarbonyl-2-hydroxyheptanoate to give the title compound (460 mg, 28% 2 steps) as a colorless liquid.

Sources & evidence

ORD record: ord-8bfaccc60487445692eef4d34d3f5887
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492550B2

Reaction notes

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