Triphenylphosphine → N-Boc-Imino-(triphenyl)phosphorane

HRID 1504266Notes

Reaction equation

HRID 1504266 reaction equation
[C:1]([N:8]=[N+]=[N-])(=[O:7])[O:2][C:3]([CH3:6])([CH3:5])[CH3:4].[C:11]1([P:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(OCC)C>[C:24]1([P:17]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:8][C:1]([O:2][C:3]([CH3:6])([CH3:5])[CH3:4])=[O:7])[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 61256Carbonazidic acid, 1,1-dimethylethyl ester

Product 1

HCID 2756802N-Boc-Imino-(triphenyl)phosphorane

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To the solution of t-butyl carbonazidate in diethyl ether, 49.6 g (0.189 mol) of triphenylphosphine was added in small portions under cooling with ice, and the reaction solution was stirred at room temperature for 1 hour, and the precipitated solid was collected by filtration, washed with 200 mL of hexane and dried under reduced pressure to give 67 g of the desired product as white crystals.

Workup

  1. temperatureunder cooling with ice
  2. filtrationthe precipitated solid was collected by filtration
  3. washwashed with 200 mL of hexane
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-441a21346bfd4125b00f912dba81f7fb
Source dataset
uspto-grants-2015_12
Patent number
US09212348B2

Reaction notes

Loading…