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

HRID 30452

反応式

HRID 30452 の反応式
[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

参加物

7

反応物 3

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

生成物 2

HCID 222Ammonia収率 1%HCID 44515770Methyl 6-(piperidin-1-ylmethyl)nicotinate収率 148.2%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

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%).

後処理

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

出典と根拠

ORDレコード
ord-0f2d767c6c3c4174915665f9ecb1aee8
出典データセット
uspto-grants-2008_09
特許番号
US07423147B2

関連ノート

読み込み中…