4-Methyl-2-oxovaleric acid → (R)-2-hydroxy-4-methylpentanoic acid

HRID 1636205Notes

Reaction equation

HRID 1636205 reaction equation
[Na].[CH3:2][CH:3]([CH3:10])[CH2:4][C:5](=[O:9])[C:6]([OH:8])=[O:7].Cl>>[OH:9][C@H:5]([CH2:4][CH:3]([CH3:10])[CH3:2])[C:6]([OH:8])=[O:7]

Participants

4

Reactant 3

HCID 704-Methyl-2-oxovaleric acidHCID 313Hydrochloric AcidHCID 5360545Sodium

Product 1

HCID 439960(R)-2-hydroxy-4-methylpentanoic acidYield 87%

Procedure

The sodium salt of 4-methyl-2-oxo-pentanoic acid 7 (152 mg, 1 mmol), RLB2HADH (13.8 mg, 276 U), HCl (1 ml, 1 mmol, 1 eq.). A reaction time of 24 hours gave 8 (114 mg, 0.87 mmol, 87% yield, >99.5% e.e.); δH1 (270 MHz) ppm: 6.63 (1H, br s, 2-OH), 4.29 (1H, br t, J=6.5 Hz, 2-H), 1.95-1.85 (1H, m, 4-H), 1.64-1.60 (2H, m, 3-H2), 0.98-0.95 (6H, 2×s, 5-H3 and 5'-H3).

Workup

  1. customA reaction time of 24 hours gave 8 (114 mg, 0.87 mmol, 87% yield, >99.5% e.e.)

Sources & evidence

ORD record
ord-7a52d0f009d54dc897542acc9066ee66
Source dataset
uspto-grants-2000_03
Patent number
US06033882

Reaction notes

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