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

HRID 1017276ノート

反応式

HRID 1017276 の反応式
[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

参加物

6

反応物 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

生成物 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]収率 81%

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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%)

出典と根拠

ORDレコード
ord-d108e9e0cf9a4cf391721ba9720aa8cf
出典データセット
uspto-grants-2002_11
特許番号
US06479486B2

反応ノート

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