Pyridine → ethyl 7,8,9,10-tetrahydro-6H-benzo[b]cyclohepta[d]furan-2-ylcarbamate

HRID 1819921Notes

Reaction equation

HRID 1819921 reaction equation
Cl[C:2]([O:4][CH2:5][CH3:6])=[O:3].[CH:7]1[C:15]2[C:14]3[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:13]=3[O:12][C:11]=2[CH:10]=[CH:9][C:8]=1[NH2:21].N1C=CC=CC=1>C(#N)C.C(OCC)(=O)C>[CH:7]1[C:15]2[C:14]3[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][C:13]=3[O:12][C:11]=2[CH:10]=[CH:9][C:8]=1[NH:21][C:2](=[O:3])[O:4][CH2:5][CH3:6]

Participants

6

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 128848837,8,9,10-tetrahydro-6H-benzo[b]-cyclohepta[d]furan-2-ylamine

Product 1

HCID 23725142ethyl 7,8,9,10-tetrahydro-6H-benzo[b]cyclohepta[d]furan-2-ylcarbamateYield 97.6%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

Ethyl chloroformate (0.16 mL, 1.6 mmol) was added to a solution of 7,8,9,10-tetrahydro-6H-benzo[b]-cyclohepta[d]furan-2-ylamine (0.30 g, 1.5 mmol) and pyridine (0.36 mL, 4.5 mmol) in acetonitrile (20 mL). The reaction mixture was stirred overnight at room temperature. The crude material was diluted in ethyl acetate and washed with water, dried (MgSO4) and concentrated. The solid was washed with hexane to provide ethyl 7,8,9,10-tetrahydro-6H-benzo[b]cyclohepta[d]furan-2-ylcarbamate (0.40 g). MS (ESI) m/z 274; Profiled 100% purity, m/z 274.1 ([M+H]+), 2.5 min, Anal. Calcd. for C16H,9NO3: C, 70.31; H, 7.01; N, 5.12. Found: C, 70.18; H, 6.95; N, 5.01.

Workup

  1. washwashed with water
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. washThe solid was washed with hexane

Sources & evidence

ORD record
ord-6facfde5b00d4e228425d7cbf8c4204d
Source dataset
uspto-grants-2009_10
Patent number
US07601856B2

Reaction notes

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