HCID 57137252, compound → HCID 57044005, compound

HRID 982189Notes

Reaction equation

HRID 982189 reaction equation
[C:1]([O:5][CH2:6][C@@H:7]([OH:19])[CH2:8][C:9](=[O:18])[CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])([CH3:4])([CH3:3])[CH3:2]>CO>[C:1]([O:5][CH2:6][C@@H:7]([OH:19])[CH2:8][C@@H:9]([OH:18])[CH2:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 57137252HCID 57137252, compound

Product 1

HCID 57044005HCID 57044005, compoundYield 70.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
30 °C

Procedure

In a 100 ml-volume egg plant type flask equipped with a three-way cock whose atmosphere had been displaced with nitrogen was charged 15 mg (0.009 mmole) of Ru2Cl4 ((R)-BINAP)2 (NEt3), and 500 mg (1.75 mmole) of t-butyl (5S)-6-t-butoxy-5-hydroxy-3-oxohexanoate as synthesized in Example 4 and 60 ml of methanol were added thereto to form a solution. The solution was transferred to a 100 ml-volume autoclave whose atmosphere had been displaced with nitrogen and stirred at 30° C. for 16 hours under a hydrogen pressure of 50 kg/cm2 to conduct hydrogenation. The solvent was removed by distillation, and the residue was purified by silica gel column chromatography to obtain 340 mg (yield: 68%) of t-butyl (3R,5S)-6-t-butoxy-3,5-dihydroxyhexanoate.

Workup

  1. customIn a 100 ml-volume egg plant type flask equipped with a three-way cock whose atmosphere
  2. additionwere added
  3. customto form a solution
  4. customThe solvent was removed by distillation
  5. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9bae569ea6a84b769595bf9736a92a4a
Source dataset
uspto-grants-1991_02
Patent number
US04994602

Reaction notes

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