4,4'-Bis(1,1-dimethylethyl)-1,1'-biphenyl → HCID 90419006, compound

HRID 514810Notes

Reaction equation

C(C1C=CC(C2C=CC(C(C)(C)C)=CC=2)=CC=1)(C)(C)C.Br[CH2:22][CH:23]1[CH2:25][CH2:24]1.[O:26]=[C:27]1[CH2:32][CH2:31][N:30]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:29][CH2:28]1>C1COCC1>[CH:25]1([CH2:24][C:27]2([OH:26])[CH2:28][CH2:29][N:30]([C:33]([O:35][C:36]([CH3:38])([CH3:37])[CH3:39])=[O:34])[CH2:31][CH2:32]2)[CH2:23][CH2:22]1

Participants

Conditions

Temperature: -78 °C

Procedure

To a suspension of 4,4′-di-tert-butylbiphenyl (DTBB, 30.33 mg, 0.114 mmol) and Li (56.7 mg, 8.09 mmol) in 50 mL of anhydrous THF was added dropwise a solution of (bromomethyl)cyclopropane (307.9 mg, 2.28 mmol) and tert-butyl 4-oxopiperidine-1-carboxylate (500 mg, 2.5 mmol) in anhydrous THF (5 mL) at −78° C. under N2. The resulting mixture was stirred at −78° C. under N2 for 8 h. The reaction mixture was quenched by satd. NH4Cl solution at −78° C. The resulting mixture was extracted with EtOAc (50 mL×2). The combined organic phase was washed with brine, dried over anhy. Na2SO4 and concentrated in vacuo. Column chromatography (15% PE/EtOAc) afforded 262.5 mg of title compound as a colorless oil. 1H NMR (CHLOROFORM-d) δ: 3.90-3.78 (m, 2H), 3.25-3.12 (m, 2H), 1.60 (dd, J=9.4, 4.3 Hz, 4H), 1.48 (s, 9H), 1.42 (d, J=6.9 Hz, 2H), 0.82-0.70 (m, 1H), 0.57-0.47 (m, 2H), 0.16-0.06 (m, 2H).

Workup

customThe reaction mixture was quenched by satd
customat −78° C
extractionThe resulting mixture was extracted with EtOAc (50 mL×2)
washThe combined organic phase was washed with brine
customdried over anhy
concentrationNa2SO4 and concentrated in vacuo

Sources & evidence

ORD record: ord-2e0fa3fb56624f828c042a378341e6ce
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09108921B2

Reaction notes

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