tert-Butyl 4-formylpiperidine-1-carboxylate → HCID 18328903、化合物

HRID 1249720ノート

反応式

HRID 1249720 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.Cl.[CH3:18][C:19]1[N:24]=[C:23]([N:25]2[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]2)[CH:22]=[CH:21][N:20]=1.C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH2:14][N:28]2[CH2:29][CH2:30][N:25]([C:23]3[CH:22]=[CH:21][N:20]=[C:19]([CH3:18])[N:24]=3)[CH2:26][CH2:27]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 1514430tert-Butyl 4-formylpiperidine-1-carboxylateHCID 5003444Sodium cyanoborohydrideHCID 18328942Pyrimidine, 2-methyl-4-(1-piperazinyl)-, hydrochloride (1:2)

生成物 1

HCID 18328903HCID 18328903、化合物収率 24.1%

試薬・触媒・溶媒 1

HCID 10129899Acetic acid methanol溶媒

実験手順

To a solution of 1-(tert-butoxycarbonyl)-4-(formyl)piperidine (7.14 g) and 1-(2-methylpyrimidin-4-yl)piperazine dihydrochloride (8.38 g) in methanol/acetic acid (99:1) (150 ml) was added sodium cyanoborohydride (6.32 g) portionwise over 30 minutes and the resultant suspension stirred at arnbient temperature for 3 hours. The suspension was quenched by addition of saturated aqueous sodium bicarbonate solution and the resulting mixture extracted with ethyl acetate. The organic phase was dried (Na2SO4) and evaporated. The residue was purified by chromatography eluting with 5% methanol in dichloromethane to give 1-tert-butoxycarbonyl-4-[1-(2-methylpyrimidin-4-yl)piperazin-4-ylmethyl]piperidine (3.02 g) as a foam.

後処理

  1. customThe suspension was quenched by addition of saturated aqueous sodium bicarbonate solution
  2. extractionthe resulting mixture extracted with ethyl acetate
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. customevaporated
  5. customThe residue was purified by chromatography
  6. washeluting with 5% methanol in dichloromethane

出典と根拠

ORDレコード
ord-0ab5f0d385e94395a29e5583357d3447
出典データセット
uspto-grants-2002_01
特許番号
US06335341B1

反応ノート

読み込み中…