Methanol → Triphenylphosphine Oxide

HRID 1793178Notes

Reaction equation

HRID 1793178 reaction equation
C([O:5]C(N(C1C=CC=CC=1)[C@H](CO)C)=O)(C)(C)C.[C:19]1([P:25]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.BrN1C(=O)CCC1=O.CO>CN(C=O)C>[C:32]1([P:25](=[O:5])([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 68582369HCID 68582369, compound

Product 1

HCID 13097Triphenylphosphine OxideYield 85%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of the N-tert-butoxycarbonyl phenyl alaninol (1.42 mmol) and triphenylphosphine (2 equiv) in DMF, N-bromosuccinimide (2 equiv) was slowly added. The reaction was warmed to 50° for 15 min and then cooled to 20°. Methanol (0.5 mL) was added to destroy the excess reagent. After 5 min, ether was added, and the ether layer was washed with water, saturated sodium carbonate, and saturated NaCl and then evaporated to a solid under high vacuum. The product was extracted twice into hexane, leaving a residue of triphenylphosphine oxide. After evaporation of the solvent, the residue was again triturated with hexane to afford the 1-Bromo-2-(tert-butoxycarbonyl)amino-3-phenyl propane:

Workup

  1. temperatureThe reaction was warmed to 50° for 15 min
  2. temperaturecooled to 20°
  3. customto destroy the excess reagent
  4. additionether was added
  5. washthe ether layer was washed with water, saturated sodium carbonate, and saturated NaCl
  6. customevaporated to a solid under high vacuum
  7. extractionThe product was extracted twice into hexane

Sources & evidence

ORD record
ord-b9585db531774ec3bb0a2d3c2eeb1d60
Source dataset
uspto-grants-2006_07
Patent number
US07078537B2

Reaction notes

Loading…