Sodium Carbonate → 3-Amino-1-(difluoro(phenyl)methyl)cyclohexanol

HRID 530857ノート

反応式

HRID 530857 の反応式
[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]1

参加物

6

反応物 4

HCID 10340Sodium CarbonateHCID 64774Pyridine, hydrofluoride (1:1)HCID 11137142Nitrilooxonium tetrafluoroborateHCID 866982403-(tert-Butoxycarbonylamino)-1-(2-phenyl-1,3-dithiaN-2-yl)cyclohexyl acetate

生成物 1

HCID 679829183-Amino-1-(difluoro(phenyl)methyl)cyclohexanol

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

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.

後処理

  1. custombubbling
  2. filtrationThe mixture and the methanol washings were filtered
  3. concentrationThe filtrate was concentrated

出典と根拠

ORDレコード
ord-65284a7fb5fa4bbfb615f31bcae26a91
出典データセット
uspto-grants-2016_05
特許番号
US09351965B2

反応ノート

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