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Sodium Sulfate → 1,1-Dimethylethyl 4-{[(5-chloro-6-methyl-3-pyridinyl)methyl]amino}-1-piperidinecarboxylate

HRID 420734
ノート
印刷プレビュー

反応式

HRID 420734 の反応式
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[Cl:15][C:16]1[CH:17]=[C:18]([CH:23]=O)[CH:19]=[N:20][C:21]=1[CH3:22].[O-]S([O-])(=O)=O.[Na+].[Na+].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])(O)=O.[Na+]>ClCCCl>[Cl:15][C:16]1[CH:17]=[C:18]([CH2:23][NH:1][CH:2]2[CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]2)[CH:19]=[N:20][C:21]=1[CH3:22]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 5

HCID 24436Sodium SulfateHCID 516892Sodium BicarbonateHCID 12682914-Amino-1-Boc-piperidineHCID 5049666Sodium triacetoxyborohydrideHCID 580017625-chloro-6-methyl-3-Pyridinecarboxaldehyde

生成物 1

HCID 580017711,1-Dimethylethyl 4-{[(5-chloro-6-methyl-3-pyridinyl)methyl]amino}-1-piperidinecarboxylate
収率 94%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

反応条件

温度
90 °C

実験手順

A solution of 1,1-dimethylethyl 4-amino-1-piperidinecarboxylate (11.19 g, 55.9 mmol), 5-chloro-6-methyl-3-pyridinecarbaldehyde (for a synthesis see WO2006/137485 A1 Example 256) (7.82 g, 50.3 mmol) and Na2SO4 (8.73 g, 61.5 mmol) in DCE (200 ml) was stirred at 90° C. for 4.5 h and at room temperature overnight. NaBH(OAc)3 (35.5 g, 168 mmol) was added portionwise for 7 h until imine was not detected by LCMS analysis. 10% NaHCO3 was added and the organic phase was extracted twice with DCM, washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure to give 1,1-dimethylethyl 4-{[(5-chloro-6-methyl-3-pyridinyl)methyl]amino}-1-piperidinecarboxylate (18.7 g, 94%) as a yellow oil.

後処理

  1. extractionthe organic phase was extracted twice with DCM
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-aba675aa3f3d4a04939c0bf9b5a4a113
出典データセット
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08097628B2

反応ノート

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