Methyl chloroformate → Methyl cyclopentyl(4-methoxyphenethyl)carbamate

HRID 404977Notes

Reaction equation

HRID 404977 reaction equation
[CH3:1][O:2][C:3]1[CH:16]=[CH:15][C:6]([CH2:7][CH2:8][NH:9][CH:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:5][CH:4]=1.C(N(CC)CC)C.Cl[C:25]([O:27][CH3:28])=[O:26]>C(OCC)C>[CH:10]1([N:9]([CH2:8][CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:16][CH:15]=2)[C:25](=[O:26])[O:27][CH3:28])[CH2:11][CH2:12][CH2:13][CH2:14]1

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 28445893N-[2-(4-methoxyphenyl)ethyl]cyclopentanamine

Product 1

HCID 66799542Methyl cyclopentyl(4-methoxyphenethyl)carbamateYield 86%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of N-(4-methoxyphenethyl)cyclopentanamine (0.827 g, 3.77 mmol) in diethyl ether was added triethylamine (0.83 mL, 5.66 mmol) and methyl chloroformate (0.44 mL, 5.66 mmol) at 0° C. The reaction mixture was gradually warmed to room temperature and stirred for 30 min. Filtration and concentration of mixture under reduced pressure gave the crude product which was purified by silica gel column chromatography using hexanes/ethyl acetate to provide the product (0.898 g, 86%) as light yellow oil. 1H NMR (400 MHz, CDCl3): δ 7.10 (d, 2H, J=8.6 Hz), 6.81 (d, 211, J=8.6 Hz), 4.32-4.12 (m, 1H), 3.76 (s, 3H), 3.69 (s, 3H), 3.24 (t, 2H, J=7.9 Hz), 2.76 (t, 2H, J=7.9 Hz), 1.79-1.76 (m, 2H), 1.67-1.66 (m, 2H), 1.54-1.47 (m, 4H). LC-MS (ESI) Calcd for C16H23NO3 [M+H]+: 278.17. Found: 278.00.

Workup

  1. filtrationFiltration and concentration of mixture under reduced pressure
  2. customgave the crude product which
  3. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-0688ecf911d947b38ddf5cde4f3d3917
Source dataset
uspto-grants-2014_06
Patent number
US08748632B2

Reaction notes

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