HCID 20306565, compound → 3-Methoxycarbonylmethyl-2-t-butoxycarbonyl-2-(2-pentynyl)-cyclopentanol

HRID 46550Notes

Reaction equation

HRID 46550 reaction equation
[C:1]([O:5][C:6]([C:8]1([CH2:19][C:20]#[C: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].[H-].[Al+3].[Li+].[H-].[H-].[H-]>CO>[CH3:18][O:17][C:15]([CH2:14][CH:9]1[CH2:10][CH2:11][CH:12]([OH:13])[C:8]1([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])[CH2:19][C:20]#[C:21][CH2:22][CH3:23])=[O:16]

Participants

4

Reactant 2

HCID 20306565HCID 20306565, compound2×HCID 21226445Aluminium lithium hydride

Product 1

HCID 203875893-Methoxycarbonylmethyl-2-t-butoxycarbonyl-2-(2-pentynyl)-cyclopentanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 5.5 g quantity of 5-t-butoxycarbonyl-4-methoxycarbonylmethyl-5-(2-pentynyl)-2-cyclopentenone (compound (2-a)) and 1.5 g of lithium aluminum hydride are dissolved in 200 ml of methanol, and the solution is refluxed in a nitrogen atmosphere for one hour. The same procedure as in Example 1 is thereafter followed, giving 3-methoxycarbonylmethyl-2-t-butoxycarbonyl-2-(2-pentynyl)-cyclopentanol (compound (1-a), R1 =t-butyl, R2 =CH3) in a yield of 93.4%, b.p. 80°-86° C./0.02 mm Hg.

Workup

  1. temperaturethe solution is refluxed in a nitrogen atmosphere for one hour

Sources & evidence

ORD record
ord-5ecac6949aa942f58da99e26754e28a3
Source dataset
uspto-grants-1979_11
Patent number
US04173707

Reaction notes

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