Imidazole → tert-butyl 1-tosyl-2,3-dihydro-1H-benzo[b]azepin-4-ylcarbamate

HRID 2389550Notes

Reaction equation

O[CH:2]1[CH:8]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:7][CH2:6][N:5]([S:17]([C:20]2[CH:26]=[CH:25][C:23]([CH3:24])=[CH:22][CH:21]=2)(=[O:19])=[O:18])[C:4]2[CH:27]=[CH:28][CH:29]=[CH:30][C:3]1=2.N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.II>C1(C)C=CC=CC=1.C(OCC)C>[S:17]([N:5]1[CH2:6][CH2:7][C:8]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[CH:2][C:3]2[CH:30]=[CH:29][CH:28]=[CH:27][C:4]1=2)([C:20]1[CH:21]=[CH:22][C:23]([CH3:24])=[CH:25][CH:26]=1)(=[O:18])=[O:19]

Participants

Conditions

Temperature: 110 °C

Procedure

To a solution of tert-butyl 5-hydroxy-1-tosyl-2,3,4,5-tetrahydro-1H-benzo[b]azepin-4-ylcarbamate (200 mg, 0.46 mmol) and imidazole (94 mg, 1.38 mmol) in toluene (10 mL), triphenylphosphine (242 mg, 262 mmol) and iodine (237 mg, 0.092 mol) were added. The reaction mixture was heated to 110° C. for 3 h. The reaction mixture was cooled to room temperature and diluted with diethyl ether (50 mL). The precipitate that formed was filtered off and the filtrate washed with water followed by a saturated solution of sodium thiosulphate, a saturated solution of sodium bicarbonate and brine. The organic layer was dried over anhydrous sodium sulfate and evaporated under vacuo to give tert-butyl 1-tosyl-2,3-dihydro-1H-benzo[b]azepin-4-ylcarbamate (20 mg, 10.4%).

Workup

temperatureThe reaction mixture was cooled to room temperature
customThe precipitate that formed
filtrationwas filtered off
washthe filtrate washed with water
dry with materialThe organic layer was dried over anhydrous sodium sulfate
customevaporated under vacuo

Sources & evidence

ORD record: ord-576c712788814c178d559161a7615dec
Source dataset: uspto-grants-2012_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08273754B2

Reaction notes

Loading…