Benzo(B)Thiophene → 9-Benzo[b]thiophen-2-yl-3-aza-spiro[5.5]undec-8-ene

HRID 419276Notes

Reaction equation

[Li]CCCC.[S:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[CH:8]=[CH:7]1.C(OC([N:22]1[CH2:27][CH2:26][C:25]2([CH2:32][CH2:31][C:30](=O)[CH2:29][CH2:28]2)[CH2:24][CH2:23]1)=O)(C)(C)C>C(OCC)C>[S:6]1[C:7]([C:30]2[CH2:31][CH2:32][C:25]3([CH2:26][CH2:27][NH:22][CH2:23][CH2:24]3)[CH2:28][CH:29]=2)=[CH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]1=2

Participants

Conditions

Temperature: -78 °C

Procedure

Was prepared according to method A with the following variation: n-BuLi (1.6 M in hexanes (4 mL, 6.4 mmol)) was added drop-wise to a solution of benzothiophene (778 mg, 5.80 mL) in diethyl ether (10 mL). The reaction was warmed to reflux for 1 h and then cooled to −78° C. 9-Oxo-3-aza-spiro[5.5]undecane-3-carboxylic acid tert-butyl ester (500 mg, 1.87 mmol) in diethyl ether was added drop-wise and the mixture was stirred at −78° C. for 2 h. Mp. 107.3-110.2° C.

Workup

customWas prepared
temperatureThe reaction was warmed
temperatureto reflux for 1 h

Sources & evidence

ORD record: ord-9ef8e67af83c4986972bb82a153306d7
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08093388B2

Reaction notes

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