Sodium Carbonate → 3-Amino-1-(difluoro(phenyl)methyl)cyclohexanol
Reaction equation
[F:1][B-](F)(F)F.N#[O+].N1C=CC=CC=1.[FH:14].C([O:18][C:19]1([C:33]2([C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)SCCCS2)[CH2:24][CH2:23][CH2:22][CH:21]([NH:25]C(OC(C)(C)C)=O)[CH2:20]1)(=O)C.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[NH2:25][CH:21]1[CH2:22][CH2:23][CH2:24][C:19]([C:33]([F:1])([F:14])[C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)([OH:18])[CH2:20]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of nitrosonium tetrafluoroborate (1.1 mmol, 128.5 mg) and hydrogen fluoride pyridine (0.5 mL) in DCM (2 mL) at 0° C. under argon was added a solution of 3-(tert-butoxycarbonylamino)-1-(2-phenyl-1,3-dithiaN-2-yl)cyclohexyl acetate (0.5 mmol, 226 mg) in DCM dropwise. The reaction mixture was stirred at 0° C. for 1 hour. Sodium carbonate (solid) was added until no further gas bubbling. The mixture and the methanol washings were filtered. The filtrate was concentrated. 3-Amino-1-(difluoro(phenyl)methyl)cyclohexanol was obtained after purification by reverse phase HPLC.
Workup
- custombubbling
- filtrationThe mixture and the methanol washings were filtered
- concentrationThe filtrate was concentrated
Sources & evidence
- ORD record
- ord-65284a7fb5fa4bbfb615f31bcae26a91
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09351965B2
Reaction notes
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