2,4-Dihydroxybenzaldehyde → 4-[((3S)-1-tert-butoxycarbonyl-3-pyrrolidinyl)oxy]-2-hydroxybenzaldehyde

HRID 53999

반응식

HRID 53999 반응식
[OH:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[C:11]([O:15][C:16]([N:18]1[CH2:22][CH2:21][C@@H:20](O)[CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:11]([O:15][C:16]([N:18]1[CH2:22][CH2:21][C@H:20]([O:10][C:8]2[CH:7]=[CH:6][C:3]([CH:4]=[O:5])=[C:2]([OH:1])[CH:9]=2)[CH2:19]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

참가 물질

5

반응물 3

HCID 72132,4-DihydroxybenzaldehydeHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 6544479tert-Butyl (3R)-3-hydroxypyrrolidine-1-carboxylate

생성물 1

HCID 570351144-[((3S)-1-tert-butoxycarbonyl-3-pyrrolidinyl)oxy]-2-hydroxybenzaldehyde수율 39.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

in 40 ml of tetrahydrofuran were dissolved 1.38 g of 2,4-dihydroxybenzaldehyde, 1.87 g of (3R)-1-tert-butoxycarbonyl-3-hydroxypyrrolidine and 2.88 g of triphenylphosphone. The thus prepared solution was mixed with 1.91 g of diethyl azodicarboxylate and stirred at room temperature for 1 hour. After distilling off the solvent, the resulting residue was purified by subjecting it to silica gel column chromatography, thereby obtaining 1.2 g of 4-[((3S)-1-tert-butoxycarbonyl-3-pyrrolidinyl)oxy]-2-hydroxybenzaldehyde in a viscous and oily form.

후처리

  1. distillationAfter distilling off the solvent
  2. customthe resulting residue was purified

출처 및 근거

ORD 기록
ord-df11f5c2e534419381a6e2930bd28079
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05620991

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