Sodium borohydride → HCID 71060655、化合物

HRID 1036721ノート

反応式

HRID 1036721 の反応式
[CH2:1]([O:3][C:4]([C:6]1([CH:19]([C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[CH2:20][N+:21]([O-])=O)[CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]1)=[O:5])[CH3:2].[BH4-].[Na+]>CO.O.O.O.O.O.O.[Ni](Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1([CH:19]([C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)[CH2:20][NH2:21])[CH2:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:16])[CH3:17])=[O:13])[CH2:7]1)=[O:5])[CH3:2]

参加物

5

反応物 2

HCID 4311764Sodium borohydrideHCID 710602643-(2-Nitro-1-pyridin-3-yl-ethyl)-piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester

生成物 1

HCID 71060655HCID 71060655、化合物

試薬・触媒・溶媒 2

HCID 11791229Dichloronickel;hexahydrate触媒HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

To a solution of 3-(2-Nitro-1-pyridin-3-yl-ethyl)piperidine-1,3-dicarboxylic acid 1-tert-butyl ester 3-ethyl ester (2.92 g, 7.17 mmol) in MeOH (60 ml) was added nickel chloride hexahydrate (1.70 g, 7.17 mmol) and the mixture was cooled in an ice bath. Sodium borohydride (1.08 g, 28.7 mmol) was portionwise added over 30 minutes and the resulting suspension was stirred for further 30 minutes at 0° C. The reaction was quenched with saturated NH4Cl solution (30 ml) and MeOH was removed in vacuo. The aqueous residue was extracted with EtOAc (2×50 ml) and DCM (2×50 ml). The combined organic extracts were dried (MgSO4) and concentrated in vacuo to afford the title compound which was used without further purification.

後処理

  1. temperaturethe mixture was cooled in an ice bath
  2. customThe reaction was quenched with saturated NH4Cl solution (30 ml) and MeOH
  3. customwas removed in vacuo
  4. extractionThe aqueous residue was extracted with EtOAc (2×50 ml) and DCM (2×50 ml)
  5. dry with materialThe combined organic extracts were dried (MgSO4)
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-90e0f6b24ce448d680f4bcfe663dea0d
出典データセット
uspto-grants-2013_10
特許番号
US08546416B2

反応ノート

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