Ethanol → HCID 11822048, compound

HRID 2186490Notes

Reaction equation

HRID 2186490 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13](=[O:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C>CCN(CC)CC>[CH2:1]([O:8][C:9]([NH:11][CH2:12][C@@H:13]([OH:20])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 702EthanolHCID 10265597Ethyl 4-{[(benzyloxy)carbonyl]amino}-3-oxobutanoate

Product 1

HCID 11822048HCID 11822048, compoundYield 106.4%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In a 200 ml autoclave were charged 40 g (0.13 mol) of ethyl 4-benzyloxycarbonylamino-3-oxobutyrate, 120 ml of ethanol, and 173 mg (0.102 mmol) of Ru2Cl4((R)-Tol-BINAP)2.NEt3, and asymmetric hydrogenation was carried out at 50° C. under a hydrogen pressure of 30 torr. for 17 hours (conversion: 98.4%; optical purity: 94%e.e.). Ethanol was evaporated under reduced pressure to furnish 38.9 g of the title compound as liquid. An aliquot of the product was purified to find that the yield was 91%.

Workup

  1. customwas carried out at 50° C. under a hydrogen
  2. customEthanol was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e4f86c82e5314df6abb9c873c3182e16
Source dataset
uspto-grants-2002_06
Patent number
US06403804B1

Reaction notes

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