Phthalimide → HCID 58951233, compound

HRID 46156Notes

Reaction equation

HRID 46156 reaction equation
N(C(OCC)=O)=NC(OCC)=O.[Si:13]([O:30][C@H:31]1[CH2:36][C@H:35]2[CH2:37][C@@H:32]1[CH2:33][C@H:34]2O)([C:26]([CH3:29])([CH3:28])[CH3:27])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[C:39]1(=[O:49])[NH:43][C:42](=[O:44])[C:41]2=[CH:45][CH:46]=[CH:47][CH:48]=[C:40]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Si:13]([O:30][C@H:31]1[CH2:36][C@H:35]2[CH2:37][C@@H:32]1[CH2:33][C@@H:34]2[N:43]1[C:39](=[O:49])[C:40]2[C:41](=[CH:45][CH:46]=[CH:47][CH:48]=2)[C:42]1=[O:44])([C:26]([CH3:29])([CH3:27])[CH3:28])([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 58951276HCID 58951276, compound

Product 1

HCID 58951233HCID 58951233, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of diethyl azodicarboxylate (2.58 mL, 16.4 mmol) in anhydrous THF (10.0 mL) was added dropwise to a mixture of (1R,2R,4R,5S)-5-(tert-butyldiphenylsilyloxy)bicyclo[2.2.1 ]heptan-2-ol (5.00 g, 13.6 mmol), phthalimide (2.31 g, 15.7 mmol), and triphenyl phosphine (4.11 g, 15.7 mmol) in anhydrous THF (60 mL) at ambient temp. under nitrogen. After stirring for 32 h, the solvents were removed in vacuo. The residue was purified by flash column chromatography (0 to 20% of ethyl acetate in hexanes) to give the title compound as a white solid. MS m/z: 496.3 (M+H)+.

Workup

  1. customthe solvents were removed in vacuo
  2. customThe residue was purified by flash column chromatography (0 to 20% of ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-e885f66e12f2415b96407ce14b0df5c9
Source dataset
uspto-grants-2013_09
Patent number
US08541592B2

Reaction notes

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