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

HRID 46553노트

반응식

HRID 46553 반응식
[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]

참가 물질

6

반응물 2

HCID 203875893-Methoxycarbonylmethyl-2-t-butoxycarbonyl-2-(2-pentynyl)-cyclopentanol2회HCID 178418361HCID 178418361, 화합물

생성물 1

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

시약·촉매·용매 3

HCID 131709914Lindlars catalyst촉매HCID 180Acetone용매HCID 8058Hexane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-3b8e5c8f9fb64a8db9a09e33c2e6039b
출처 데이터셋
uspto-grants-1979_11
특허 번호
US04173707

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