Ethyl Acetate → HCID 18601029, compound

HRID 638629Notes

Reaction equation

HRID 638629 reaction equation
[H][H].C([O:10][CH2:11][C@@H:12]1[C@@H:16]([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:15][CH2:14][C@H:13]1[OH:21])C1C=CC=CC=1.C(OCC)(=O)C>[C].[Pd].C(O)(=O)C>[CH2:17]([C@H:16]1[CH2:15][CH2:14][C@@H:13]([OH:21])[C@@H:12]1[CH2:11][OH:10])[CH2:18][CH2:19][CH3:20]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 56633302HCID 56633302, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18601029HCID 18601029, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

In an atmosphere of hydrogen, a mixture of 4.29 g of (1R,2S,3S)-2-benzyloxymethyl-3-butylcyclopentan-1-ol (prepared in Reference Example 7), 500 ml of 10% palladium-carbon, 20 ml of ethyl acetate and 10 ml of acetic acid was stirred for 16 hrs at room temperature. After stirring the reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography on silica gel using a mixture of cyclohexane and ethyl acetate (1:3) as eluent to give 2.59 g of the title compound having the following physical characteristics in a 91.8% yield.

Workup

  1. stirringAfter stirring the reaction mixture
  2. filtrationwas filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by column chromatography on silica gel using
  5. additiona mixture of cyclohexane and ethyl acetate (1:3) as eluent

Sources & evidence

ORD record
ord-fb9d690f0aa141d28244f65812180ad3
Source dataset
uspto-grants-1985_12
Patent number
US04562207

Reaction notes

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