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

1 g (4.04 mmol) of tert-butyl 2,3-dihydro-1H-benzo[e][1,4]diazepine-4(5H)-carboxylate was dissolved in 20 mL of dichloromethane and treated with 1.54 mL (8.86 mL) of triethylamine followed by 0.53 mL (4.83 mmol) of 3-methylbut-2-enoyl chloride. The reaction mixture was stirred over night at room temperature, poured onto water (50 mL) and extracted three times with 50 mL of dichloromethane each. The organic phases were combined, washed with a saturated solution of sodium chloride, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica (eluent: 5-10% methanol in dichloromethane) to yield 1.27 g of the title compound as a white solid.

1. additionpoured onto water (50 mL)
2. extractionextracted three times with 50 mL of dichloromethane each
3. washwashed with a saturated solution of sodium chloride
4. dry with materialdried over magnesium sulfate
5. concentrationconcentrated in vacuo
6. customThe residue was purified by column chromatography on silica (eluent: 5-10% methanol in dichloromethane)

ORD record

ord-b7b66118fd10492088c5f4a6bcbb7448

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09169253B2