tert-butyl 1-(3-methylbut-2-enoyl)-2,3-dihydro-1H-benzo[e][1,4]diazepine-4(5H)-carboxylate → tert-butyl 8,8-dimethyl-6-oxo-3,4,7,8-tetrahydro-1H-[1,4]diazepino[6,7,1-ij]quinoline-2(6H)-carboxylate

HRID 1754541Notes

Reaction equation

HRID 1754541 reaction equation
[CH3:1][C:2]([CH3:24])=[CH:3][C:4]([N:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[CH2:10][N:9]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:8][CH2:7]1)=[O:5]>[Hg]>[CH3:1][C:2]1([CH3:24])[C:13]2[C:12]3=[C:11]([CH2:10][N:9]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:8][CH2:7][N:6]3[C:4](=[O:5])[CH2:3]1)[CH:16]=[CH:15][CH:14]=2

Participants

3

Reactant 1

HCID 86712747tert-butyl 1-(3-methylbut-2-enoyl)-2,3-dihydro-1H-benzo[e][1,4]diazepine-4(5H)-carboxylate

Product 1

HCID 86712748tert-butyl 8,8-dimethyl-6-oxo-3,4,7,8-tetrahydro-1H-[1,4]diazepino[6,7,1-ij]quinoline-2(6H)-carboxylateYield 61.1%

Reagents, catalysts & solvents 1

HCID 23931MercuryCatalyst

Procedure

A solution of 0.33 g (1.0 mmol) of tert-butyl 1-(3-methylbut-2-enoyl)-2,3-dihydro-1H-benzo[e][1,4]diazepine-4(5H)-carboxylate of step 1.1 was irradiated with a 150 W mercury lamp in a immersion well reactor with a pyrex filter in 20 mL of acetone until completion of the reaction monitored by liquid chromatography. The solution was concentrated in vacuo and the residue was purified by column chromatography on silica (eluent: 10-30% ethyl acetate in heptane) to yield 202 mg of the title compound as a beige solid.

Workup

  1. filtrationfilter in 20 mL of acetone until completion of the reaction
  2. concentrationThe solution was concentrated in vacuo
  3. customthe residue was purified by column chromatography on silica (eluent: 10-30% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-9110e5e19b7f437b86b2780d6c91a2ce
Source dataset
uspto-grants-2015_10
Patent number
US09169253B2

Reaction notes

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