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

HRID 46552ノート

反応式

HRID 46552 の反応式
[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]

参加物

5

反応物 3

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 70583183HCID 70583183、化合物2 回

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-30bd3dcd32d94d62ae595d45f6e97e2f
出典データセット
uspto-grants-1979_11
特許番号
US04173707

反応ノート

読み込み中…