3-Methoxycarbonylmethyl-2-t-butoxycarbonyl-2-(2-pentynyl)-cyclopentanol → 2-Tert-butoxycarbonyl-3-methoxycarbonylmethyl-2-(cis-2-pentenyl)-cyclopentanol

HRID 46553ノート

反応式

HRID 46553 の反応式
[CH3:1][O:2][C:3]([CH2:5][CH:6]1[CH2:10][CH2:9][CH:8]([OH:11])[C:7]1([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:12][C:13]#[C:14][CH2:15][CH3:16])=[O:4].[H][H]>[Pd].CC([O-])=O.CC([O-])=O.[Pb+2].CCCCCC.CC(C)=O>[C:20]([O:19][C:17]([C:7]1([CH2:12]/[CH:13]=[CH:14]\[CH2:15][CH3:16])[CH:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])[CH2:10][CH2:9][CH:8]1[OH:11])=[O:18])([CH3:21])([CH3:23])[CH3:22]

参加物

6

反応物 2

HCID 203875893-Methoxycarbonylmethyl-2-t-butoxycarbonyl-2-(2-pentynyl)-cyclopentanol2 回HCID 178418361HCID 178418361、化合物

生成物 1

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

試薬・触媒・溶媒 3

HCID 131709914Lindlars catalyst触媒HCID 180Acetone溶媒HCID 8058Hexane溶媒

実験手順

A 1.4 g quantity of 3-methoxycarbonylmethyl-2-methoxycarbonyl-2-(2-pentynyl)-cyclopentanol (compound (1-a)) and 2.2 g of Lindlar catalyst are dissolved in a mixture of 50 ml of n-hexane and 5 ml of acetone. The starting compound is thus reduced at room temperature and atmospheric pressure with use of hydrogen gas. The reaction is completed when the solution has absorbed the theoretical amount of the gas, whereupon the catalyst is filtered off. The filtrate is concentrated in vacuo, and the residue dissolved in benzene-ethyl acetate and purified with a silica gel column. The product is distilled in a vacuum, giving 2-methoxycarbonyl-3-methoxycarbonylmethyl-2-(cis-2-pentenyl)-cyclopentanol (compound (1-b), R1 =R2 =CH3) in a yield of 87%, b.p. 74°-78° C./0.01 mm Hg.

後処理

  1. customis thus reduced at room temperature
  2. customhas absorbed the theoretical amount of the gas
  3. filtrationwhereupon the catalyst is filtered off
  4. concentrationThe filtrate is concentrated in vacuo
  5. dissolutionthe residue dissolved in benzene-ethyl acetate
  6. custompurified with a silica gel column
  7. distillationThe product is distilled in a vacuum

出典と根拠

ORDレコード
ord-3b8e5c8f9fb64a8db9a09e33c2e6039b
出典データセット
uspto-grants-1979_11
特許番号
US04173707

反応ノート

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