Allyl bromide → HCID 15147735, compound

HRID 1416622Notes

Reaction equation

HRID 1416622 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[CH2:7][OH:8].[CH2:9](Br)[CH:10]=C.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH2:1]([N:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[CH2:7][OH:8])[CH:9]=[CH2:10]

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 8471TriethylamineHCID 643492(2S)-1-Methyl-2-pyrrolidinemethanol

Product 1

HCID 15147735HCID 15147735, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

(S)-1-methyl-2-pyrrolidinemethanol (5.10 g, 50 mmol, Aldrich Chemical Co.) was dissolved in 50 mL of CHCl3, then 5.25 mL of allyl bromide and 8.34 mL of triethylamine were added. The reaction mixture was stirred at room temperature for 2 hours, then the volatiles were removed under reduced pressure. The residue was purified by chromatography on silica gel to give 6.3 g of the title product. MS (DCI/NH3) m/e: 142 (M+H)+. 1H NMR (CDCI3, 300 MHz) δ: 6.05-5.90 (m, 1H), 5.33-5.17 (m, 2H), 3.77-3.68 (m, 1H), 3.58-3.47 (m, 2H), 3.32-3.20 (m, 1H), 3.16-3.05 (m, 1H), 2.90-2.78 (m, 1H), 2.53-2.40 (m, 1H), 2.02-1.73 (m, 4H).

Workup

  1. customthe volatiles were removed under reduced pressure
  2. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-c1556efea887430186b6b8f1fd496035
Source dataset
uspto-grants-1999_06
Patent number
US05914328

Reaction notes

Loading…