Sodium triacetoxyborohydride → HCID 18338589, compound

HRID 2298503Notes

Reaction equation

[C:1]([O:5][C:6]([CH2:8][CH2:9][CH2:10][C:11](=[O:16])[C:12]([O:14][CH3:15])=[O:13])=[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][CH2:10][CH:11]([OH:16])[C:12]([O:14][CH3:15])=[O:13])=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

Reactant 3

HCID 5049666Sodium triacetoxyborohydride

HCID 18338590HCID 18338590, compound

HCID 18338591HCID 18338591, compound

Product 1

HCID 18338589HCID 18338589, compoundYield 78.2%

Procedure

Crude methyl 5-tert-butoxycarbonyl-2-oxopentanoate (1.08 g, 4.7 mmol) and sodium triacetoxyborohydride (1.0 g, 4.7 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 (854 mg, 78%, 2 steps) as a colorless liquid.

Sources & evidence

ORD record: ord-e3099403744d498da84b38d55f7c3a26
Source dataset: uspto-grants-2002_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06492550B2

Reaction notes

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