Triethylamine → (2S,3R)-methyl-2-benzamidomethyl-3-hydroxybutyrate

HRID 2186492Notes

Reaction equation

HRID 2186492 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH:4]([CH2:8][NH:9][C:10](=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5](=[O:7])[CH3:6].CCN(CC)CC>C(Cl)Cl>[C:10]([NH:9][CH2:8][C@@H:4]([C@H:5]([OH:7])[CH3:6])[C:3]([O:2][CH3:1])=[O:18])(=[O:17])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 11831808Methyl 2-((benzoylamino)methyl)-3-oxobutanoate

Product 1

HCID 10060699(2S,3R)-methyl-2-benzamidomethyl-3-hydroxybutyrateYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 100 ml autoclave was put a solution of 2.5 g (10 mmol) of methyl-2-(N-benzoylamino)methyl-3-oxobutyrate and 173 mg (0.102 mmol) of Ru2Cl4((R)-BINAP)2.NEt3 in 17.5 ml of methylene chloride, and the mixture was stirred at 50° C. under a hydrogen pressure of 10000 kPa for 20 hours. The solvent was removed by evaporation under reduced pressure, and the residue was purified by column chromatography to furnish 2.25 g (90%) of the title compound. Optical purity: 98%e.e.

Workup

  1. customThe solvent was removed by evaporation under reduced pressure
  2. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-0d3ab2c3eb3b43be9d54cb0bcb994bc8
Source dataset
uspto-grants-2002_06
Patent number
US06403804B1

Reaction notes

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