Allyl bromide → HCID 15147735, compound

HRID 617329Notes

Reaction equation

HRID 617329 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 63 g of the title product. MS (DCI/NH3) m/e: 142 (M+H)+. 1H NMR (CDCl3, 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-3c6b2726f6b3443fb2c8e59be5d40010
Source dataset
uspto-grants-1999_09
Patent number
US05948793

Reaction notes

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