Binap, (A+-)- → HCID 15034949, compound

HRID 703277Notes

Reaction equation

HRID 703277 reaction equation
[C:1]([NH:4][CH2:5][CH:6]([C:12](=[O:14])[CH3:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:3])[CH3:2].C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(Cl)Cl>[C:1]([NH:4][CH2:5][C@@H:6]([C@H:12]([OH:14])[CH3:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 634876Binap, (A+-)-HCID 15034948HCID 15034948, compound

Product 1

HCID 15034949HCID 15034949, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 100 ml-volume stainless steel autoclave whose atmosphere had been displaced with nitrogen was added a solution of 2.01 g (10 mmole) of ethyl 2-(N-acetylamino)methyl-3-oxobutanoate and 168 mg (0.1 mmole) of ##STR11## ((+)-BINAP) in 15 ml of methylene chloride, and a reaction was conducted at 70 ° C. under a hydrogen pressure of 130 kg/cm2 for 30 hours. The reaction mixture was concentrated, and the residue was purified by silica gel chromatography using a 7/3 (by volume) mixture of hexane and isopropanol as an eluent to give 1.7 g (yield: 85%) of ethyl (2S, 3R)-2-(N-acetylamino)methyl-3-hydroxybutanoate having an optical purity of 93 %ee as determined in the same manner as in Example 2.

Workup

  1. customwas conducted at 70 ° C. under a hydrogen
  2. customfor 30 hours
  3. concentrationThe reaction mixture was concentrated
  4. customthe residue was purified by silica gel chromatography
  5. additiona 7/3 (by volume) mixture of hexane and isopropanol as an eluent

Sources & evidence

ORD record
ord-6ddd272e43d54fc0b5e0763c708e7660
Source dataset
uspto-grants-1991_01
Patent number
US04981992

Reaction notes

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