Benzyl chloroformate → Benzyl (9-oxo-6,7,8,9-tetrahydro-5H-benzo[7]annulen-2-yl)carbamate

HRID 1027909Notes

Reaction equation

HRID 1027909 reaction equation
[NH2:1][C:2]1[CH:13]=[CH:12][C:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10](=[O:11])[C:4]=2[CH:3]=1.C([O-])([O-])=O.[K+].[K+].Cl[C:21]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22]>CO.C(Cl)Cl>[O:11]=[C:10]1[C:4]2[CH:3]=[C:2]([NH:1][C:21](=[O:22])[O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:13]=[CH:12][C:5]=2[CH2:6][CH2:7][CH2:8][CH2:9]1

Participants

6

Reactant 3

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 2668073-amino-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one

Product 1

HCID 69226242Benzyl (9-oxo-6,7,8,9-tetrahydro-5H-benzo[7]annulen-2-yl)carbamate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of Example 128A (1.63 g, 9.30 mmol) and K2CO3 (2.57 g, 18.60 mmol) in MeOH (10 ml) under nitrogen atmosphere was cooled to 0° C. The mixture was treated with benzyl chloroformate (1.726 ml, 12.09 mmol), raised to room temperature and stirred for 16 hours. The mixture was diluted with CH2Cl2, washed with water, dried and concentrated under reduced pressure. The residue was purified by chromatography on silica gel eluting with 15% EtOAc/hexanes to provide the title product. 1H NMR (CDCl3) δ 1.75-1.90 (m, 4H), 2.67-2.75 (m, 2H), 2.84-2.92 (m, 2H), 4.70 (d, J=5.76 Hz, 2H), 6.72 (s, 1H), 7.16 (d, J=8.14 Hz, 1H), 7.36-7.39 (m, 5H), 7.49 (d, J=2.71 Hz, 1H), 7.70 (d, J=7.12 Hz, 1H). MS (M+NH4)+ m/z 327.

Workup

  1. washwashed with water
  2. customdried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by chromatography on silica gel eluting with 15% EtOAc/hexanes

Sources & evidence

ORD record
ord-a5fca3bcaf30458f837b11ea2e733ac7
Source dataset
uspto-grants-2014_05
Patent number
US08735411B2

Reaction notes

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