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

HRID 1017276Notes

Reaction equation

HRID 1017276 reaction equation
[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

Participants

6

Reactant 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

Product 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]Yield 81%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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%)

Sources & evidence

ORD record
ord-d108e9e0cf9a4cf391721ba9720aa8cf
Source dataset
uspto-grants-2002_11
Patent number
US06479486B2

Reaction notes

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