Hexane → HCID 59382868, compound

HRID 1254270Notes

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-8180b9025a144000853fd13f3a4f6eea
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455521B2

Reaction notes

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