HCID 131718338, compound → HCID 56618511, compound

HRID 1975511Notes

Reaction equation

HRID 1975511 reaction equation
[CH2:1]([O:8][CH2:9][C@@H:10]([O:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][O:24]1)[CH2:11][C:12](=[O:21])[CH2:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO>[CH2:1]([O:8][CH2:9][C@@H:10]([O:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][O:24]1)[CH2:11][C@@H:12]([OH:21])[CH2:13][C:14]([O:16][C:17]([CH3:19])([CH3:20])[CH3:18])=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 131718338HCID 131718338, compound2×

Product 1

HCID 56618511HCID 56618511, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 2.0 ml of methanol was dissolved 1.0 g (2.55 mmol) of tert-butyl (S)-6-benzyloxy-3-oxo-5-tetrahydropyranyloxyhexanoate of formula (2) obtained in Reference Example 5 and the enantioselective hydrogenation reaction was carried out as in Example 1 using Ru2Cl4 [(R)-Tol-BINAP]2N(CH2CH3)3 of formula (3) for 18 hours with stirring under a hydrogen pressure of 30 kg/cm2 and at a reaction temperature of from 35° to 40° C. After the reaction was over, the solvent was recovered and the residue formed was purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate 85/15 by volume) to provide 350 mg (0.89 mmol, percent yield 35%) of tert-butyl (3R,5S)-6-benzyloxy-3-hydroxy-5-tetahydropyranyloxyhexanoate of formula (1) as a colorless transparent liquid.

Workup

  1. customobtained in Reference Example 5
  2. customthe enantioselective hydrogenation reaction
  3. customof from 35° to 40° C
  4. customwas recovered
  5. customthe residue formed
  6. customwas purified by silica gel column chromatography (developing solvent: n-hexane/ethyl acetate 85/15 by volume)

Sources & evidence

ORD record
ord-faef29a6029046d7a5dc506464e44d25
Source dataset
uspto-grants-1994_02
Patent number
US05286883

Reaction notes

Loading…