Azetidine → HCID 15725070, compound

HRID 982308Notes

Reaction equation

HRID 982308 reaction equation
[NH:1]1[CH2:4][CH2:3][CH2:2]1.Br[CH2:6][C:7]#[C:8][CH2:9][N:10]([CH3:15])[C:11](=[O:14])[O:12][CH3:13]>>[CH3:13][O:12][C:11](=[O:14])[N:10]([CH2:9][C:8]#[C:7][CH2:6][N:1]1[CH2:4][CH2:3][CH2:2]1)[CH3:15]

Participants

3

Reactant 2

HCID 10422AzetidineHCID 15065538HCID 15065538, compound

Product 1

HCID 15725070HCID 15725070, compound

Procedure

A solution of methyl[4-(diethylamino)-2-butynyl]- methyl-carbamate (4.2 g, 0.02 mol) (Example 1i) in anhydrous diethyl ether (50 ml) is added dropwise at room temperature to a stirred solution of cyanogen bromide in anhydrous diethyl ether (40 ml). The mixture is allowed to stand for 12 hours and the diethyl ether layer is separated, washed with water (40 ml), dried over magnesium sulfate, and concentrated. The resulting oil is then purified by bulb to bulb distillation under high vacuum to give methyl N-(4-bromo-2-butynyl)-N-methylcarbamate as a ight yellow oil. Azetidine (2 g, 0.032 mol) is added to a stirred solution of methyl N-(4-bromo-2-butynyl)-N-methylcarbamate (3.6 g, 0.016 mol). The mixture is kept at room temperature for one hour and then filtered. The filtrate is concentrated and the resulting oil purified by bulb to bulb distillation under high vacuum to give a light yellow oil. NMR(CDCl3): 4.10 (brs, 2H); 3.7 (s, 3H); 3.39 (brs, 2H); 2.94 (s, 3H); 2.45 (brs, 4H).

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate is concentrated
  3. distillationthe resulting oil purified by bulb to bulb distillation under high vacuum
  4. customto give a light yellow oil

Sources & evidence

ORD record
ord-44d7818107b748109cfb672a88a3eb7c
Source dataset
uspto-grants-1991_02
Patent number
US04996201

Reaction notes

Loading…