Hexane → HCID 59382868, compound

HRID 2355390Notes

Reaction equation

Br[C:2]1([Cl:14])[CH2:7][CH:6]=[CH:5][CH:4]=[C:3]1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[Li]CCCC.CCCCCC.CON(C)[C:29]([C@@H:31]1[CH2:36][CH2:35][CH2:34][N:33]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH2:32]1)=[O:30]>C1COCC1>[C:40]([O:39][C:37]([N:33]1[CH2:34][CH2:35][CH2:36][C@@H:31]([C:29](=[O:30])[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:14])[CH2:32]1)=[O:38])([CH3:43])([CH3:42])[CH3:41]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of 2-bromo-2-chloro-biphenyl (5.34 g, 20 mmol) in anhydrous THF (50 mL) cooled to −78° C. was added dropwise a solution of 1.6 M n-BuLi in hexane (12.5 mL, 20 mmol). The reaction mixture was stirred at −78° C. for 1 h and a solution of (R)-tert-butyl 3-(N-methoxy-N-methylcarbamoyl)-piperidine-1-carboxylate (5.44 g, 20 mmol) in anhydrous THF (50 mL) was added. The mixture was allowed to warm to rt and stirred overnight. The mixture was quenched with sat'd aq NH4Cl (100 mL) and extracted with EtOAc (3×75 mL). The combined organic layers were dried over Na2SO4 and concentrated to give the crude product, which was purified by flash column chromatography to afford (3R)-1-(tert-butoxycarbonyl)-3-((2-(2-chlorophenyl))benzoyl)piperidine (4.43 g, 55%).

Workup

temperatureto warm to rt
stirringstirred overnight
customThe mixture was quenched with sat'd aq NH4Cl (100 mL)
extractionextracted with EtOAc (3×75 mL)
dry with materialThe combined organic layers were dried over Na2SO4
concentrationconcentrated
customto give the crude product, which
customwas purified by flash column chromatography

Sources & evidence

ORD record: ord-3d8edd46f4c44d4bbe984bdf418b60cf
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07754737B2

Reaction notes

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