Acetic Acid → 2-Tert-butoxycarbonyl-3-methoxycarbonylmethyl-2-(cis-2-pentenyl)-cyclopentanol

HRID 46552Notes

Reaction equation

HRID 46552 reaction equation
[C:1]([O:5][C:6]([C:8]1([CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH3:23])[C:12](=[O:13])[CH:11]=[CH:10][CH:9]1[CH2:14][C:15]([O:17][CH3:18])=[O:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].C(O)(=O)C>CO>[C:1]([O:5][C:6]([C:8]1([CH2:19]/[CH:20]=[CH:21]\[CH2:22][CH3:23])[CH:9]([CH2:14][C:15]([O:17][CH3:18])=[O:16])[CH2:10][CH2:11][CH:12]1[OH:13])=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 70583183HCID 70583183, compound2×

Product 1

HCID 706014122-Tert-butoxycarbonyl-3-methoxycarbonylmethyl-2-(cis-2-pentenyl)-cyclopentanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 740 mg quantity of 5-tert-butoxycarbonyl-4-methoxycarbonylmethyl-5-(cis-2-pentenyl)-2-cyclopentenone (compound (2-b)) and 120 mg of sodium borohydride are dissolved in 100 ml of methanol, and the solution is refluxed for one hour. On completion of the reaction, 2 ml of acetic acid is added to the reaction mixture. The resulting mixture is concentrated in a vacuum. The residue is distilled in a vacuum, giving 2-tert-butoxycarbonyl-3-methoxycarbonylmethyl-2-(cis-2-pentenyl)-cyclopentanol (compound (1-b), R1 =t-Bu, R2 =CH3) in a yield of 98.5%, b.p. 75°-79° C./0.005 mm Hg.

Workup

  1. temperaturethe solution is refluxed for one hour
  2. additionis added to the reaction mixture
  3. concentrationThe resulting mixture is concentrated in a vacuum
  4. distillationThe residue is distilled in a vacuum

Sources & evidence

ORD record
ord-30bd3dcd32d94d62ae595d45f6e97e2f
Source dataset
uspto-grants-1979_11
Patent number
US04173707

Reaction notes

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