Ethyl 4-piperidinecarboxylate → 1-[3-(4-Chloro-benzoylamino)-benzyl]-piperidine-4-carboxylic acid ethyl ester

HRID 1486720ノート

反応式

HRID 1486720 の反応式
[Cl:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([CH:15]=O)[CH:10]=2)=[O:7])=[CH:4][CH:3]=1.[NH:19]1[CH2:29][CH2:28][CH:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:21][CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[CH2:26]([O:25][C:23]([CH:22]1[CH2:28][CH2:29][N:19]([CH2:15][C:11]2[CH:12]=[CH:13][CH:14]=[C:9]([NH:8][C:6](=[O:7])[C:5]3[CH:17]=[CH:18][C:2]([Cl:1])=[CH:3][CH:4]=3)[CH:10]=2)[CH2:20][CH2:21]1)=[O:24])[CH3:27]

参加物

6

反応物 4

HCID 70770Ethyl 4-piperidinecarboxylateHCID 516892Sodium BicarbonateHCID 23750934-chloro-N-(3-formylphenyl)benzamideHCID 5049666Sodium triacetoxyborohydride

生成物 1

HCID 867065481-[3-(4-Chloro-benzoylamino)-benzyl]-piperidine-4-carboxylic acid ethyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 4-chloro-N-(3-formyl-phenyl)-benzamide (2.1 g, 8.09 mmol), ethyl isonipecotate (1.53 g, 9.55 mmol) in DCM (45 mL) is treated with sodium triacetoxy borohydride (2.5 g, 11.2 mmol) in 5 portions over 20 min. and the reaction mixture is stirred for 18 h at RT. Aq. sat. NaHCO3 (20 mL) is added and the mixture is stirred for 30 min. The phases are separated and the aqueous phase is extracted twice with DCM (50 ml). The combined organic phases are dried over MgSO4 and evaporated. The title compound is obtained as a colorless solid (3.24 g, 98%); LC-MS A: tR=0.72 min; [M+H]+=401.01.

後処理

  1. stirringthe mixture is stirred for 30 min
  2. customThe phases are separated
  3. extractionthe aqueous phase is extracted twice with DCM (50 ml)
  4. dry with materialThe combined organic phases are dried over MgSO4
  5. customevaporated

出典と根拠

ORDレコード
ord-a6b022559d5d4fa896cf050db2c9f0fe
出典データセット
uspto-grants-2016_08
特許番号
US09428456B2

反応ノート

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