Sodium bis(trimethylsilyl)amide → tert-Butyl 3-(4-aminophenyl)azetidine-1-carboxylate

HRID 1919096Notes

Reaction equation

I[CH:2]1[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]1.[NH2:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Na+].N[C@H]1CCCC[C@H]1O>C(O)(C)C>[NH2:13][C:14]1[CH:19]=[CH:18][C:17]([CH:2]2[CH2:5][N:4]([C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])[CH2:3]2)=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of tert-butyl 3-iodoazetidine-1-carboxylate (1 g, 3.53 mmol), 4-aminophenylboronic acid (630 mg, 4.59 mmol), NiI2 (66 mg, 0.212 mmol), NaHMDS (1.94 g, 10.6 mmol), (1R,2S)-2-aminocyclohexanol (24 mg, 0.212 mmol) in isopropanol (8 mL) was stirred at 150° C. in microwave for 2 h. It was then evaporated and the residue was dissolved with water and ethyl acetate. The water phase was separated and extracted with ethyl acetate. The combined extracts were dried over sodium sulfate and concentrated under reduced pressure. The residue was purified with column chromatography to give 298a (360 mg, 40%). MS: [M+H]+ 249.

Workup

customIt was then evaporated
dissolutionthe residue was dissolved with water and ethyl acetate
customThe water phase was separated
extractionextracted with ethyl acetate
dry with materialThe combined extracts were dried over sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified with column chromatography

Sources & evidence

ORD record: ord-e09953a953564a3fb1a163176382d031
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618107B2

Reaction notes

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