Methyl chloroformate → HCID 50994819, compound

HRID 404982Notes

Reaction equation

HRID 404982 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:14]=[CH:15][CH:16]=1)[CH2:6][CH2:7][NH:8][CH:9]1[CH2:13][CH2:12][CH2:11][CH2:10]1.C(N(CC)CC)C.Cl[C:25]([O:27][CH3:28])=[O:26]>C(OCC)C>[CH:9]1([N:8]([CH2:7][CH2:6][C:5]2[CH:14]=[CH:15][CH:16]=[C:3]([O:2][CH3:1])[CH:4]=2)[C:25](=[O:26])[O:27][CH3:28])[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 28814460HCID 28814460, compound

Product 1

HCID 50994819HCID 50994819, compoundYield 84.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of N-(3-methoxyphenethyl)cyclopentanamine (1.31 g, 6 mmol) in diethyl ether (50 mL) was added triethylamine (1.3 mL, 9 mmol) and methyl chloroformate (0.7 mL, 9 mmol) at 0° C. The reaction mixture was gradually warmed to room temperature and stirred for 30 min. Filtration and removal of solvent under reduced pressure followed by silica gel column chromatography using hexanes/ethyl acetate afforded methyl cyclopentyl(3-methoxyphenethyl)-carbamate as a pale yellow liquid (1.41 g, 84%). 1H NMR (400 MHz, CDCl3): δ 7.19 (t, 1H, J=7.6 Hz), 6.78-6.73 (overlapping doublets and singlet, 3H), 4.27-4.24 (m, 1H), 3.78 (s, 3H), 3.70 (s, 3H), 3.28 (t, 2H, J=7.9 Hz), 2.80 (t, 2H, J=7.9 Hz), 1.68-1.67 (m, 2H), 1.53-1.50 (m, 6H). LC-MS (ESI) Calcd for C16H23NO3 [M+H]+: 278.17. Found: 278.00.

Workup

  1. filtrationFiltration and removal of solvent under reduced pressure

Sources & evidence

ORD record
ord-6e849e7b914a40b09440de8f0bc006d3
Source dataset
uspto-grants-2014_06
Patent number
US08748632B2

Reaction notes

Loading…