Ethanol → ethyl(S)-4-benzyloxy-3-hydroxybutyrate

HRID 2186487Notes

Reaction equation

HRID 2186487 reaction equation
[CH2:1]([O:8][CH2:9][C:10](=[O:17])[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C>CCN(CC)CC>[CH2:1]([O:8][CH2:9][C@@H:10]([OH:17])[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 9813448Ethyl 4-(benzyloxy)-3-oxobutanoate

Product 1

HCID 8030429ethyl(S)-4-benzyloxy-3-hydroxybutyrateYield 89.2%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In a 100 ml autoclave were charged 20.0 g (84.7 mmol) of ethyl 4-benzyloxy-3-oxobutyrate, 16 ml of ethanol, and 31 mg (0.034 mmol) of Ru2Cl4((R)-Tol-BINAP)2.NEt3, and asymmetric hydrogenation was performed at 100° C. under a hydrogen pressure of 10 torr for 3 hours (conversion: 100%). The solvent was evaporated under reduced pressure to give 18.0 g of the title compound as liquid.

Workup

  1. customwas performed at 100° C. under a hydrogen
  2. customfor 3 hours
  3. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ca77b06782de47f4b75b0f22a750a77f
Source dataset
uspto-grants-2002_06
Patent number
US06403804B1

Reaction notes

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