Triphenylphosphine → HCID 18940749, compound

HRID 356072Notes

Reaction equation

HRID 356072 reaction equation
[Br:1]N1C(=O)CCC1=O.[C:9]([N:16]([CH2:21][CH3:22])[CH2:17][CH2:18][CH2:19]O)([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(Cl)Cl>[C:9]([N:16]([CH2:17][CH2:18][CH2:19][Br:1])[CH2:21][CH3:22])([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10]

Participants

5

Reactant 3

HCID 11776TriphenylphosphineHCID 67184N-bromobutanimideHCID 23092014tert-Butyl ethyl3-hydroxypropylcarbamate

Product 1

HCID 18940749HCID 18940749, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

11 g (0.0618 mol) of N-bromosuccinimide are added in the course of 5 minutes, with stirring, to a solution, which has been cooled to 0° C., of 10.49 g (0.0516 mol) of 3-(N-BOC-ethylamino)-1-propanol and 16.23 g (0.0619 mol) of triphenylphosphine in 160 ml of methylene chloride. The reaction mixture is stirred for a further 30 minutes at 0°-20° C. and is then concentrated by evaporation in vacuo. The dark-colored oily residue is stirred with 200 ml of hexane, whereupon a brown precipitate forms. After filtration and concentration of the filtrate by evaporation in vacuo, the title compound is obtained in the form of an oil, Rf value=0.71 (silica gel/tert-butyl methyl ether).

Workup

  1. stirringThe reaction mixture is stirred for a further 30 minutes at 0°-20° C.
  2. concentrationis then concentrated by evaporation in vacuo
  3. stirringThe dark-colored oily residue is stirred with 200 ml of hexane, whereupon a brown precipitate forms
  4. filtrationAfter filtration and concentration of the filtrate
  5. customby evaporation in vacuo

Sources & evidence

ORD record
ord-cbec98ad126d4d1299de25392abf95c1
Source dataset
uspto-grants-1998_11
Patent number
US05834486

Reaction notes

Loading…