Triethylamine → HCID 57044005, compound

HRID 982192Notes

Reaction equation

HRID 982192 reaction equation
CCN(CC)CC.[C:8]([O:12][CH2:13][C@@H:14]([OH:26])[CH2:15][C:16](=[O:25])[CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])([CH3:11])([CH3:10])[CH3:9].[H][H]>C(O)C>[C:8]([O:12][CH2:13][C@@H:14]([OH:26])[CH2:15][C@@H:16]([OH:25])[CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])([CH3:11])([CH3:9])[CH3:10]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 57137252HCID 57137252, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57044005HCID 57044005, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In the same manner as in Example 5, 15 mg (0.009 mmole) of Ru2Cl4 ((R)-BINAP)2 (NEt3) was weighed, and 500 mg (1.75 mmole) of t-butyl (5S)-6-t-butoxy-5-hydroxy-3-oxohexanoate as synthesized in Example 4 and 50 ml of ethanol 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 the solution was stirred at 30° C. for 16 hours at 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 (diethyl ether/hexane: 5/1 by volume) to obtain 300 mg (yield: 60%) of t-butyl (3R,5S)-6-t-butoxy-3,5-dihydroxyhexanoate.

Workup

  1. additionwere added
  2. customto form a solution
  3. customThe solvent was removed by distillation
  4. customthe residue was purified by silica gel column chromatography (diethyl ether/hexane: 5/1 by volume)

Sources & evidence

ORD record
ord-d16138c8c45544ec907effa67bf22d7f
Source dataset
uspto-grants-1991_02
Patent number
US04994602

Reaction notes

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