Potassium bis(trimethylsilyl)amide → 7-Methylene-5-(1-phenyl-ethyl)-3b,4,5,6,6a,7-hexahydro-1-thia-5-aza-cyclopenta[alpha]pentalene

HRID 1013411Notes

Reaction equation

[CH3:1][Si]([N-][Si](C)(C)C)(C)C.[K+].[C:11]1([CH:17]([N:19]2[CH2:30][CH:22]3[C:23]4[CH:24]=[CH:25][S:26][C:27]=4[C:28](=O)[CH:21]3[CH2:20]2)[CH3:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1.ClCCl>[CH2:1]=[C:28]1[C:27]2[S:26][CH:25]=[CH:24][C:23]=2[CH:22]2[CH2:30][N:19]([CH:17]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH3:18])[CH2:20][CH:21]12

Participants

Conditions

Temperature: 0 °C

Procedure

Potassium bis(trimethylsilyl)amide (308 mg, 1.55 mmol) was added to a solution of methyl triphenylphosphonium bromide (575 mg, 1.61 mmol) in 7 mL of THF at 0° C. After 30 minutes of stirring at 0° C., the product from step e) (303 mg, 1.07 mmol) dissolved in 2 mL of THF was added to the reaction mixture and was allowed to come to room temperature over 1 hour. The reaction mixture was diluted with dichloromethane (30 mL) and was washed with brine, dried (MgSO4) and concentrated to an oil. The crude was purified by column chromatography (SiO2) using 5-55% ethylacetate-hexane gradient to afford the subtitle compound (226 mg, yield: 74.8%). MS calculated for C18H19NS +H: 282, observed: 282.

Workup

additionwas added to the reaction mixture
waitto come to room temperature over 1 hour
washwas washed with brine
dry with materialdried (MgSO4)
concentrationconcentrated to an oil
customThe crude was purified by column chromatography (SiO2)

Sources & evidence

ORD record: ord-da514198d41d45a5acd28392d41e7174
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981919B2

Reaction notes

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