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

HRID 420734
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HRID 420734 반응식
[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]
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참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

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온도
90 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-aba675aa3f3d4a04939c0bf9b5a4a113
출처 데이터셋
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08097628B2

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