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Sodium triacetoxyborohydride → 4-([Methyl-(2-pyridin-4-ylpyrimidin-4-ylmethyl)amino]methyl}piperidine-1-carboxylic acid tert-butyl ester

HRID 1921913
ノート
印刷プレビュー

反応式

HRID 1921913 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][NH:15][CH3:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:17]1[CH:22]=[CH:21][C:20]([C:23]2[N:28]=[C:27]([CH:29]=O)[CH:26]=[CH:25][N:24]=2)=[CH:19][CH:18]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:15]([CH3:16])[CH2:29][C:27]2[CH:26]=[CH:25][N:24]=[C:23]([C:20]3[CH:19]=[CH:18][N:17]=[CH:22][CH:21]=3)[N:28]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 5049666Sodium triacetoxyborohydrideHCID 21934652tert-Butyl 4-((methylamino)methyl)piperidine-1-carboxylateHCID 534417682-Pyridin-4-YL-pyrimidine-4-carbaldehyde

生成物 1

HCID 115603394-([Methyl-(2-pyridin-4-ylpyrimidin-4-ylmethyl)amino]methyl}piperidine-1-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane
溶媒

実験手順

To a solution of 4-methylaminomethylpiperidine-1-carboxylic acid tert-butyl ester (37 mg, 0.16 mmol) in anhydrous CH2Cl2 (3 mL) was added 2-pyridin-4-yl-pyrimidine-4-carbaldehyde (Preparation 2, 30 mg, 0.16 mmol) followed by NaBH(OAc)3 (38 mg, 0.18 mmol). The mixture was stirred vigorously at rt for 24 h, before being partitioned between CH2Cl2 (30 mL) and H2O (20 mL). The aqueous phase was extracted with CH2Cl2 (20 mL), then the combined organics were washed with brine (20 mL), dried (MgSO4), filtered and concentrated in vacuo. Flash column chromatography (EtOAc) gave the title compound. RT=2.36 min; m/z (ES+)=398 [M+H]+.

後処理

  1. custombefore being partitioned between CH2Cl2 (30 mL) and H2O (20 mL)
  2. extractionThe aqueous phase was extracted with CH2Cl2 (20 mL)
  3. washthe combined organics were washed with brine (20 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-4428db75a4794b72a76bd77038264b5e
出典データセット
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08173807B2

反応ノート

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