Piperidine → Methyl 6-(piperidin-1-ylmethyl)nicotinate

HRID 30452

반응식

HRID 30452 반응식
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]=O)=[N:6][CH:5]=1.[NH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.[OH-].[Na+]>[NH3:6].[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][N:13]2[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[N:6][CH:5]=1

참가 물질

7

반응물 3

HCID 8082PiperidineHCID 586269Methyl 6-formylpyridine-3-carboxylateHCID 5049666Sodium triacetoxyborohydride

생성물 2

HCID 222Ammonia수율 1%HCID 44515770Methyl 6-(piperidin-1-ylmethyl)nicotinate수율 148.2%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 14798Sodium Hydroxide용매

실험 절차

To a solution of 6-formyl-nicotinic acid methyl ester (0.200 g, 1.21 mmol) and piperidine (0.14 mL, 1.33 mmol) in DCM (15 mL) was added NaB(OAc)3H (0.380 g, 1.80 mmol). After 18 h, the reaction was diluted with 1 N NaOH (10 mL) and extracted with DCM (2×50 mL). The organic layers were combined, dried (Na2SO4), and concentrated. Chromatography of the residue (SiO2; 1-3% 2 M NH3 in MeOH/DCM) gave the title compound as an oil (0.210 g, 74%).

후처리

  1. extractionextracted with DCM (2×50 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-0f2d767c6c3c4174915665f9ecb1aee8
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423147B2

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