Phthalimide → HCID 57826870, compound

HRID 1967086Notes

Reaction equation

HRID 1967086 reaction equation
O[CH:2]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[C:38]1(=[O:48])[NH:42][C:41](=[O:43])[C:40]2=[CH:44][CH:45]=[CH:46][CH:47]=[C:39]12.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[O:43]=[C:41]1[C:40]2[C:39](=[CH:47][CH:46]=[CH:45][CH:44]=2)[C:38](=[O:48])[N:42]1[CH:2]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:3][NH:4][C:5](=[O:11])[O:6][C:7]([CH3:10])([CH3:9])[CH3:8]

Participants

6

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 15224543tert-Butyl (2-hydroxy-3-phenylpropyl)carbamate

Product 1

HCID 57826870HCID 57826870, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1,1-dimethylethyl (2-hydroxy-3-phenylpropyl)carbamate (10.0 g, 39.8 mmol), PPh3 (12.5 g, 47.8 mmol) and phthalimide (6.44 g, 43.8 mmol) in THF (125 mL) at RT was added DEAD (9.4 mL, 59.7 mmol) over 5 min. After 1 h at RT, the reaction solution was concentrated and purified on silica (hexanes/EtOAc, 2:1) to give the title compound as a white solid (12.6 g, 83%): LCMS (ES) m/z 381 (M+H)+.

Workup

  1. concentrationthe reaction solution was concentrated
  2. custompurified on silica (hexanes/EtOAc, 2:1)

Sources & evidence

ORD record
ord-d1f01df1818b430f8249d428a9afdc91
Source dataset
uspto-grants-2013_04
Patent number
US08420690B2

Reaction notes

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