Potassium bis(trimethylsilyl)amide → HCID 57701073, compound

HRID 422882Notes

Reaction equation

C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH2:11]([O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]2([C:33]3[C:38]([F:39])=[CH:37][CH:36]=[CH:35][C:34]=3F)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][C:26]2=[O:32])=[CH:21][CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1(C)C=CC=CC=1.CN1C(=O)N(C)CCC1>[CH2:11]([O:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]23[CH2:31][CH2:30][CH2:29][CH2:28][CH:27]=[C:26]2[O:32][C:34]2[CH:35]=[CH:36][CH:37]=[C:38]([F:39])[C:33]3=2)=[CH:23][CH:24]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 90 °C

Procedure

KHMDS (0.2 mL, 0.5 M in toluene) was added to a solution of 2-(4-(benzyloxy)phenyl)-2-(2,6-difluorophenyl)cycloheptanone (50 mg) in toluene (3 mL) and DMPU (1 mL). The reaction mixture was heated at 90° C. for 2 h (TLC indicated some conversion of the starting material). Additional heating for 1 h gave no further conversion of the starting material according to TLC. The organic phase was washed with water (10 mL), brine, dried (Na2SO4) and concentrated in vacuo. Work-up by flash chromatography (eluent heptane dichloromethane 1:1) afforded the title compound 22 in a yield of 20 mg. 1H-NMR (400 MHz, CDCl3): δ ppm 7.49-7.46 (m, 2H), 7.50-7.34 (m, 5H), 7.10-7.00 (m, 1H), 6.96-6.91 (m, 2H), 6.61-6.59 (m, 1H), 6.53-6.48 (m, 1H), 5.73 (dd, J=5, 9 Hz, 1H), 5.02 (s, 2H), 3.07-3.02 (m, 1H), 2.00-1.20 (m, 8H).

Workup

temperatureAdditional heating for 1 h
customgave no further conversion of the starting material
washThe organic phase was washed with water (10 mL), brine
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-b8c75e83633d444a96e11b8dc4c5943c
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08101651B2

Reaction notes

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