Vinyl chloroformate → HCID 59694179, compound

HRID 899712Notes

Reaction equation

HRID 899712 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([CH2:13][OH:14])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:16]([O:18][CH:19]=[CH2:20])=[O:17]>ClCCCl>[CH:19]([O:18][C:16](=[O:17])[O:14][CH2:13][CH:10]1[CH2:11][CH2:12][N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:9]1)=[CH2:20]

Participants

4

Reactant 2

HCID 78808Vinyl chloroformateHCID 5176654(1-Benzylpyrrolidin-3-yl)methanol

Product 1

HCID 59694179HCID 59694179, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of (1-benzyl-pyrrolidin-3-yl)-methanol (prepared as described by Y.-H. Wu and R. F. Feldkamp, Pyrrolidines I, 1961, 26, 1519-1524) (455 mg, 2.38 mmol) and vinyl chloroformate (0.40 mL, 4.7 mmol) in 1,2-dichloroethane (10 mL) was heated to reflux for 2 h then concentrated in vacuo. Purification of the crude material by column chromatography on silica gel (5% MeOH/CH2Cl2) gave a yellow oil (440 mg, 71%). 1H NMR (CDCl3) δ 1.84 (m, 1H), 2.26 (m, 1H), 3.03 (m, 5H), 4.01 (br s, 2H), 4.23 (m, 2H), 4.61 (dd, 1H, J=6.2, 2.3 Hz), 4.93 (dd, 1H, J=14, 2.1 Hz), 7.06 (dd, 1H, J=14, 6.3 Hz), 7.41 (m, 3H), 7.53 (m, 2H).

Workup

  1. temperatureto reflux for 2 h
  2. concentrationthen concentrated in vacuo
  3. customPurification of the crude material by column chromatography on silica gel (5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-239ef321e49743969e7c49d431852c8c
Source dataset
uspto-grants-2008_04
Patent number
US07354932B2

Reaction notes

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