tert-butyl N-but-3-enyl-N-(2-oxobut-3-enyl)carbamate → tert-Butyl 3-oxo-2,3,6,7-tetrahydro-1H-azepine-1-carboxylate

HRID 523627Notes

Reaction equation

[CH2:1]([N:5]([CH2:13][C:14](=[O:17])[CH:15]=[CH2:16])[C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH2:2]C=C>C(Cl)Cl>[O:17]=[C:14]1[CH2:13][N:5]([C:6]([O:7][C:8]([CH3:9])([CH3:10])[CH3:11])=[O:12])[CH2:1][CH2:2][CH:16]=[CH:15]1

Participants

Conditions

Temperature: 18 °C

Procedure

To a mixture of tert-butyl N-but-3-enyl-N-(2-oxobut-3-enyl)carbamate (1.50 g, 6.27 mmol, 1.00 Eq) in DCM (250 mL), was added Zhan catalyst 1B (150.00 mg, 204.43 umol, 0.03 Eq) in one portion at 18° C. under N2. The mixture was stirred at 18° C. for 10 hr. TLC showed the reaction was completed. The mixture was concentrated in vacuum. The residue was purified by silica gel chromatography (PE/EA=30/1, 20/1) to afford tert-butyl 6-oxo-3,7-dihydro-2H-azepine-1-carboxylate (850.00 mg, 4.02 mmol, 64.17% yield) as yellow solid. 1H NMR (400 MHz, CHLOROFORM-d) 6.36-6.64 (m, 1H), 5.88-6.14 (m, 1H), 4.23-4.35 (m, 1H), 4.16 (s, 1H), 3.51-3.68 (m, 2H), 2.62-2.78 (m, 2H), 1.46 (d, J=17.32 Hz, 1H).

Workup

concentrationThe mixture was concentrated in vacuum
customThe residue was purified by silica gel chromatography (PE/EA=30/1, 20/1)

Sources & evidence

ORD record: ord-d0f0cc259db449b38761158c73a74920
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09339510B2

Reaction notes

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