Triphenylphosphine → HCID 68526670, compound

HRID 2246717Notes

Reaction equation

HRID 2246717 reaction equation
O[CH:2]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:3][CH2:4][N:5](C)[C:6](=O)OC(C)(C)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:39]N1C(=O)CCC1=O>C(Cl)Cl>[Br:39][CH:2]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[CH2:3][CH2:4][NH:5][CH3:6]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 10683119HCID 10683119, compound

Product 1

HCID 68526670HCID 68526670, compoundYield 22.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl [3-hydroxy-3-phenylpropyl]methylcarbamate (0.52 g, 1.96 mmol) was dissolved in CH2Cl2 (5 mL) and cooled to 0° C. Triphenylphosphine (1.02 g, 3.9 mmol) was added followed by N-bromosuccinimide (0.59 g, 3.3 mmol) and the mixture was stirred for 45 minutes. The reaction mixture was loaded directly onto silica gel and immediately purified via Isco chromatography (Redisep, silica, gradient 0-30% ethyl acetate in hexane) to afford 100 mg of (3-bromo-3-phenyl-propyl)-methyl-amine.

Workup

  1. customimmediately purified via Isco chromatography (Redisep, silica, gradient 0-30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-88b1c596b84e497ebfe8d0c88e358f83
Source dataset
uspto-grants-2010_03
Patent number
US07687529B2

Reaction notes

Loading…