Tetrahydrofuran → (1R*,2R*,5S*,6RS)-8-benzyl-6-(tert-butoxycarbonyl)-1-phenylspiro[8-azabicyclo[3.2.1]octane-2,2'(5'H)-furan]

HRID 1017276노트

반응식

HRID 1017276 반응식
[CH2:1]([N:8]1[C@@H:13]2[CH:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15][C@@:9]1([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C@:10](/[CH:24]=[CH:25]\[CH2:26]O)([OH:23])[CH2:11][CH2:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N(C(OCC)=O)=NC(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O1CCCC1>O>[CH2:1]([N:8]1[C@H:13]2[CH2:12][CH2:11][C@@:10]3([CH:24]=[CH:25][CH2:26][O:23]3)[C@:9]1([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:15][CH:14]2[C:16]([O:18][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 8028TetrahydrofuranHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 70153639(1R*,2S*,5S*,6RS)-8-Benzyl-6-(tert-butoxycarbonyl)-2-[(Z)-3-hydroxypropenyl]-1-phenyl-8-azabicyclo[3.2.1]octan-2-ol

생성물 1

HCID 70152701(1R*,2R*,5S*,6RS)-8-benzyl-6-(tert-butoxycarbonyl)-1-phenylspiro[8-azabicyclo[3.2.1]octane-2,2'(5'H)-furan]수율 81%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

The mixture of (1R*,2S*,5S*,6RS)-8-benzyl-6-(tert-butoxycarbonyl)-2-[(Z)-3-hydroxypropenyl]-1-phenyl-8-azabicylco[3.2.1]octan-2-ol (Description 26; a 3:1 mixture of C6 epimers, 4.0 g, 8.9 mmol), diethyl azodicarboxylate (1.8 ml, 11.4 mmol), triphenylphosphine (3.6 g, 13.7 mmol), tetrahydrofuran (30 ml) was stirred at room temperature for 15 minutes. The mixture was treated with water (0.1 ml) and concentrated in vacuo. The residue was treated with diethyl ether followed by iso-hexane. The solid was filtered off and the filtrate was concentrated and purified by chromatography on silica gel (iso-hexane:diethyl ether 0-20%) to give the title compound (3.1 g, 81%) as a 3:1 mixture of C6 epimers.

후처리

  1. concentrationconcentrated in vacuo
  2. additionThe residue was treated with diethyl ether
  3. filtrationThe solid was filtered off
  4. concentrationthe filtrate was concentrated
  5. custompurified by chromatography on silica gel (iso-hexane:diethyl ether 0-20%)

출처 및 근거

ORD 기록
ord-d108e9e0cf9a4cf391721ba9720aa8cf
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06479486B2

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