Vinyl chloroformate → HCID 59694099, compound

HRID 1624360Notes

Reaction equation

HRID 1624360 reaction equation
[CH:1]([O:3][C:4](=[O:19])[O:5][CH2:6][CH:7]1[CH2:11][CH2:10][N:9](CC2C=CC=CC=2)[CH2:8]1)=[CH2:2].Cl[C:21]([O:23][CH:24]=[CH2:25])=[O:22]>ClCCCl>[CH:24]([O:23][C:21]([N:9]1[CH2:10][CH2:11][CH:7]([CH2:6][O:5][C:4]([O:3][CH:1]=[CH2:2])=[O:19])[CH2:8]1)=[O:22])=[CH2:25]

Participants

4

Reactant 2

HCID 78808Vinyl chloroformateHCID 59694179HCID 59694179, compound

Product 1

HCID 59694099HCID 59694099, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of carbonic acid 1-benzyl-pyrrolidin-3-ylmethyl ester vinyl ester (440 mg, 1.68 mmol) and vinyl chloroformate (0.30 mL, 3.5 mmol) in 1,2-dichloroethane (10 mL) was heated to reflux for 6 h then concentrated in vacuo. Purification of the crude material by column chromatography on silica gel (20% EtOAc/hexanes) gave a yellow oil (335 mg, 83%). 1H NMR (CDCl3) δ 1.68-1.85 (m, 1H), 2.03-2.16 (m, 1H), 2.59-2.71 (m, 1H), 3.26 (m, 1H), 3.41-3.52 (m, 1H), 3.55-3.72 (m, 2H), 4.11-4.28 (m, 2H), 4.45 (dd, 1H, J=6.3, 1.5 Hz), 4.61 (m, 1H), 4.78 (dd, 1H, J=14, 1.5 Hz), 4.94 (m, 1H), 7.08 (m, 1H), 7.22 (dd, 1H, J=14, 6.3 Hz).

Workup

  1. temperatureto reflux for 6 h
  2. concentrationthen concentrated in vacuo
  3. customPurification of the crude material by column chromatography on silica gel (20% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d15901d13e1049a89e369ccb00fe0ffc
Source dataset
uspto-grants-2014_07
Patent number
US08778967B2

Reaction notes

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