HCID 15034950, compound → HCID 15034951, compound

HRID 703275Notes

Reaction equation

HRID 703275 reaction equation
[C:1]([NH:6][CH2:7][CH:8]([C:14](=[O:16])[CH3:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])([O:3][CH2:4][CH3:5])=[O:2]>C(Cl)Cl>[C:1]([NH:6][CH2:7][C@@H:8]([C@H:14]([OH:16])[CH3:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])([O:3][CH2:4][CH3:5])=[O:2]

Participants

3

Reactant 1

HCID 15034950HCID 15034950, compound

Product 1

HCID 15034951HCID 15034951, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 100 ml-volume stainless steel autoclave whose atmosphere had been displaced with nitrogen was added a solution of 2.31 g (10 mmole) of ethyl 2-(N-carboethoxyamino)methyl-3-oxobutanoate and 84.5 mg (0.05 mmole) of Ru2Cl4 ((+)-BINAP)2NEt3 in 18 ml of methylene chloride, and a reaction was conducted at 45° C. under a hydrogen pressure of 75 kg/cm2 for 20 hours. The reaction mixture was taken out and concentrated under reduced pressure of 20 mmHg. The concentrate was purified by silica gel chromatography using a 8/2 (by volume) mixture of hexane and isopropanol as an eluent to obtain 1.63 g (yield: 70%) of ethyl (2S, 3R)-2-(N-carboethoxyamino)methyl-3-hydroxybutanoate having an optical purity of 90 %ee as determined in the same manner as in Example 2, except for using a 1000:100:1 (by volume) mixture of hexane, tetrahydrofuran and methanol as an eluent.

Workup

  1. customwas conducted at 45° C. under a hydrogen
  2. customfor 20 hours
  3. concentrationconcentrated under reduced pressure of 20 mmHg
  4. customThe concentrate was purified by silica gel chromatography
  5. additiona 8/2 (by volume) mixture of hexane and isopropanol as an eluent

Sources & evidence

ORD record
ord-eaeadbb6a4e447c5abb35b100a2f38a3
Source dataset
uspto-grants-1991_01
Patent number
US04981992

Reaction notes

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