beta(R)-benzyloxy-alpha(RS)-phenyl-1,4-dioxaspiro[4,5]decane-2(R)-ethanol → alpha(R)-benzyl-1,4-dioxaspiro-[4,5]decane-2(R)-methanol

HRID 1721135Notes

Reaction equation

HRID 1721135 reaction equation
C([O:8][C@@H:9]([C@H:18]1[CH2:22][O:21][C:20]2([CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[O:19]1)[CH:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)O)C1C=CC=CC=1>C(O)(=O)C.[Pd]>[CH2:10]([C@H:9]([C@H:18]1[CH2:22][O:21][C:20]2([CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)[O:19]1)[OH:8])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

4

Reactant 1

HCID 22856134beta(R)-benzyloxy-alpha(RS)-phenyl-1,4-dioxaspiro[4,5]decane-2(R)-ethanol

Product 1

HCID 86749442alpha(R)-benzyl-1,4-dioxaspiro-[4,5]decane-2(R)-methanolYield 65.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

(iv)(a) A solution of 130 mg (0.35 mmol) of β(R)-benzyloxy-α(RS)-phenyl-1,4-dioxaspiro[4,5]decane-2(R)-ethanol in 3 ml of acetic acid was hydrogenated over 10% palladium-on-carbon under a pressure of about 4.1 atmospheres for 2 days. The catalyst was removed by filtration and the filtrate was evaporated. The crude product was purified by flash chromatography on silica gel using 2% methanol in dichloromethane for the elution. There were obtained 60 mg of α(R)-benzyl-1,4-dioxaspiro[4,5]decane-2(R)-methanol in the form of a colourless oil; MS: m/e 262 [M]+.

Workup

  1. customThe catalyst was removed by filtration
  2. customthe filtrate was evaporated
  3. customThe crude product was purified by flash chromatography on silica gel using 2% methanol in dichloromethane for the elution

Sources & evidence

ORD record
ord-8c7266435a1a4b0eafb70f158164f43b
Source dataset
uspto-grants-1996_04
Patent number
US05508430

Reaction notes

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