Tetrabutylammonium Fluoride → HCID 67392762, compound
Reaction equation
[Si]([O:8][CH2:9][C@@H:10]([NH:17][C@@H:18]([C:30]1[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=1)[C:19]([F:29])([F:28])[O:20][C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)[CH2:11][S:12][CH2:13][CH:14]1[CH2:16][CH2:15]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.C(OCC)C>[CH:14]1([CH2:13][S:12][CH2:11][C@H:10]([NH:17][C@@H:18]([C:30]2[CH:35]=[CH:34][C:33]([F:36])=[CH:32][CH:31]=2)[C:19]([F:28])([F:29])[O:20][C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)[CH2:9][OH:8])[CH2:16][CH2:15]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
To a solution of [2-(tert-butyldimethylsilanyloxy)-1(R)-cyclopropylmethylsulfanylmethyl-ethyl]-[2,2-difluoro-2-(4-fluorophenoxy)-1(S)-(4-fluorophenyl)ethyl]amine (1.06 g, 1.94 mmol) in dry THF (10 ml) at 0° C., a 1M solution of tetrabutylammonium fluoride (2.3 ml, 2.3 mmol) was added. After stirring for 3 h at 0° C., the reaction mixture was diluted with ethyl ether (20 ml) and washed with sat. ammonium chloride solution (20 ml), brine (10 ml) and dried over sodium sulfate. After removal of the solvent under vacuum, the crude was purified by flash chromatography using ethyl acetate/hexanes (2/8) as eluent to give 3-cyclopropylmethylsulfanyl-2(R)-[2,2-difluoro-2-(4-fluorophenoxy)-1(S)-(4-fluorophenyl)ethylamino]propan-1-ol as an oil (0.418 g, 74%).
Workup
- washwashed with sat. ammonium chloride solution (20 ml), brine (10 ml)
- dry with materialdried over sodium sulfate
- customAfter removal of the solvent under vacuum
- customthe crude was purified by flash chromatography
Sources & evidence
- ORD record
- ord-b6d17e0eafff48dab086e278dbf33a2b
- Source dataset
- uspto-grants-2011_09
- Patent number
- US08013186B2
Reaction notes
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