Sodium Bicarbonate → (2S,3S)-3-(2-methoxy-5-(trifluoromethyl)benzyl)amino-2-phenylpiperidine

HRID 1634322ノート

反応式

HRID 1634322 の反応式
Cl.Cl.[C:3]1([C@H:9]2[C@@H:14]([NH2:15])[CH2:13][CH2:12][CH2:11][NH:10]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:16][O:17][C:18]1[CH:25]=[CH:24][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:22][C:19]=1[CH:20]=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH3:16][O:17][C:18]1[CH:25]=[CH:24][C:23]([C:26]([F:27])([F:29])[F:28])=[CH:22][C:19]=1[CH2:20][NH:15][C@H:14]1[CH2:13][CH2:12][CH2:11][NH:10][C@H:9]1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

参加物

6

反応物 4

HCID 516892Sodium BicarbonateHCID 27792722-Methoxy-5-(trifluoromethyl)benzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 69654807(2S,3S)-2-Phenylpiperidin-3-amine dihydrochloride

生成物 1

HCID 9889280(2S,3S)-3-(2-methoxy-5-(trifluoromethyl)benzyl)amino-2-phenylpiperidine

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred suspension of Compound 1 (150 mg, 0.60 mmol) and Compound 4 (123 mg, 0.60 mmol) in dry CH2Cl2 (6 ml) was added NaBH(OAc)3 (179 mg, 0.84 mmol) portionwise under nitrogen at room temperature. The reaction mixture was stirred at room temperature for 3.5 hr. This was basified with sat. NaHCO3 aq., extracted with CH2Cl2, dried with MgSO4, and concentrated to give crude (2S,3S)-3-(2-methoxy-5-(trifluoromethyl)benzyl)amino-2-phenylpiperidine as a colorless oil. This was purified with chromatography to give pure (2S,3S)-3-(2-methoxy-5-(trifluoromethyl)benzyl)amino-2-phenylpiperidine as a colorless oil (95 mg). This was diluted with ethyl acetate, added HCl-MeOH, and concentrated. The white solid was recrystallized from MeOH-ether to give Compound 5 as a white crystalline (85 mg, 32.4%)

後処理

  1. extractionextracted with CH2Cl2
  2. dry with materialdried with MgSO4
  3. concentrationconcentrated

出典と根拠

ORDレコード
ord-add1c2ce350849f787391b387b1b576f
出典データセット
uspto-grants-2003_01
特許番号
US06506775B1

反応ノート

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