Ammonium Chloride → HCID 67158216, compound
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][CH:10]=[CH:11][CH:12]=2)=[CH:4][CH:3]=1.C([Li])CCC.[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH:26]1[C:31](=[O:36])N(OC)C)=[O:24])([CH3:21])([CH3:20])[CH3:19].[Cl-].[NH4+]>C1COCC1>[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][CH2:28][CH2:27][CH:26]1[C:31]([C:10]1[O:9][C:8]([C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[CH:12][CH:11]=1)=[O:36])=[O:24])([CH3:21])([CH3:20])[CH3:19]Participants
Procedure
To a stirred solution of 2-(4-fluorophenyl)-furan (1.8 g, 11.1 mmol) in THF (100 ml) at −35° C. was added n-butyl lithium (2.5M in THF) (4.54 ml, 11.4 mmol) over 3 min. The resultant mixture was stirred for 10 min. at −35° C. and then (RS)-1-(tert-butyloxycarbonyl)-2-(N-methoxy-N-methylcarbamoyl)piperidine (3.09 g, 11.4 mmol) in THF (10 ml) was added over 1 min. The resultant solution was stirred for 15 min. at −35° C. and then poured into saturated ammonium chloride (120 ml) and extracted with ethyl acetate (3×50 ml). The combined organics were washed with saturated aqueous sodium hydrogen carbonate (50 ml) and evaporated in vacuo. The residue was chromatographed on silica gel eluting with 10% ethyl acetate in hexane to give the title compound as a golden oil (3.59 g, 85%).
Workup
- extractionextracted with ethyl acetate (3×50 ml)
- washThe combined organics were washed with saturated aqueous sodium hydrogen carbonate (50 ml)
- customevaporated in vacuo
- customThe residue was chromatographed on silica gel eluting with 10% ethyl acetate in hexane
Sources & evidence
- ORD record
- ord-819c425e7ca549f383b1a4b5924496a0
- Source dataset
- uspto-grants-2011_05
- Patent number
- US07943645B2
Reaction notes
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