[(R)-1-hydroxymethyl-3-(4-hydroxy-phenyl)-1-methyl-propyl]-carbamic acid tert-butyl ester → [(R)-1-Formyl-3-(4-heptyloxy-phenyl)-1-methyl-propyl]-carbamic acid tert-butyl ester

HRID 12587

반응식

HRID 12587 반응식
[C:1]([O:5][C:6](=[O:21])[NH:7][C@:8]([CH2:19][OH:20])([CH3:18])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=1)([CH3:4])([CH3:3])[CH3:2]>C(Cl)Cl.[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC>[C:1]([O:5][C:6](=[O:21])[NH:7][C@:8]([CH:19]=[O:20])([CH3:18])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13])=[CH:13][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

참가 물질

4

반응물 1

HCID 59655583[(R)-1-hydroxymethyl-3-(4-hydroxy-phenyl)-1-methyl-propyl]-carbamic acid tert-butyl ester

생성물 1

HCID 59339517[(R)-1-Formyl-3-(4-heptyloxy-phenyl)-1-methyl-propyl]-carbamic acid tert-butyl ester

시약·촉매·용매 2

HCID 178419074HCID 178419074, 화합물촉매HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of [(R)-1-hydroxymethyl-3-(4-hydroxy-phenyl)-1-methyl-propyl]-carbamic acid tert-butyl ester (1.98 g, 5.03 mMol) in CH2Cl2 (20 ml) is added N-morpholine-N-oxide (884 mg, 7.54 mMol) and tetra-n-propylammonium perruthenate (177 mg, 0.50 mMol). The mixture is stirred at RT for 1 hour. The mixture is then filtered over a short pad of SiO2 eluting with diethyl ether. The filtrate is concentrated under reduced pressure to give the title compound. The crude product is sufficiently pure to be used in the next stage without further purification.

후처리

  1. filtrationThe mixture is then filtered over a short pad of SiO2 eluting with diethyl ether
  2. concentrationThe filtrate is concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-651db5982fa74a0abf2ef00d192ec652
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728020B2

연결된 노트

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