Sodium Hydroxide → (2S,3S)-3-(5-(1-Cyanocyclopropyl)-2-methoxybenzyl)amino-2-phenylpiperidine

HRID 481486

反応式

HRID 481486 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.[C:16]([C:18]1([C:21]2[CH:22]=[CH:23][C:24]([O:29][CH3:30])=[C:25]([CH:28]=2)[CH:26]=O)[CH2:20][CH2:19]1)#[N:17].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[Na+]>C(Cl)Cl>[C:16]([C:18]1([C:21]2[CH:22]=[CH:23][C:24]([O:29][CH3:30])=[C:25]([CH:28]=2)[CH2:26][NH:15][C@H:14]2[CH2:13][CH2:12][CH2:11][NH:10][C@H:9]2[C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:20][CH2:19]1)#[N:17]

参加物

6

反応物 4

HCID 14798Sodium HydroxideHCID 5049666Sodium triacetoxyborohydrideHCID 190664325-(1-Cyanocyclopropyl)-2-methoxybenzaldehydeHCID 69654807(2S,3S)-2-Phenylpiperidin-3-amine dihydrochloride

生成物 1

HCID 9799042(2S,3S)-3-(5-(1-Cyanocyclopropyl)-2-methoxybenzyl)amino-2-phenylpiperidine収率 41%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred suspension of Compound 3 (150 mg, 0.60 mmol) and Compound 2 (145 mg, 0.72 mmol) in dry CH2Cl2 (5 ml) was added NaBH(OAc)3 (358 mg, 1.68 mmol) portionwise at room temperature. The reaction mixture was stirred at room temperature for 6 h. The mixture was basified to pH10-11 with 10% NaOH aq. with ice-cooling. The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The combined solution was washed with brine, dried (MgSO4) and concentrated in vacuo to give crude product. The crude product (300 mg) was purified by column chromatography on silica gel with CH2Cl2 -MeOH (20:1-10:1) to give Compound 4 (89 mg, 41%) as a yellow viscous oil.

後処理

  1. temperaturecooling
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with CH2Cl2
  4. washThe combined solution was washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customto give crude product
  8. customThe crude product (300 mg) was purified by column chromatography on silica gel with CH2Cl2 -MeOH (20:1-10:1)

出典と根拠

ORDレコード
ord-eb5d9595d0754a179895ec8f0191ad83
出典データセット
uspto-grants-1998_08
特許番号
US05789423

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