(2H-1,3-benzodioxol-5-yl)boronic acid → 4-(Benzo[1,3]dioxole-5-carbonyl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 713454

反応式

HRID 713454 の反応式
[O:1]1[C:5]2[CH:6]=[CH:7][C:8](B(O)O)=[CH:9][C:4]=2[O:3][CH2:2]1.[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([C:26](SC2C=CC=CC=2)=[O:27])[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14]>C1COCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].S1C=CC=C1C([O-])=O.[Cu+]>[C:13]([O:17][C:18]([N:20]1[CH2:25][CH2:24][CH:23]([C:26]([C:8]2[CH:7]=[CH:6][C:5]3[O:1][CH2:2][O:3][C:4]=3[CH:9]=2)=[O:27])[CH2:22][CH2:21]1)=[O:19])([CH3:16])([CH3:15])[CH3:14]

参加物

6

反応物 2

HCID 2734371(2H-1,3-benzodioxol-5-yl)boronic acidHCID 893758004-Phenylsulfanylcarbonyl-piperidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 712267454-(Benzo[1,3]dioxole-5-carbonyl)-piperidine-1-carboxylic acid tert-butyl ester収率 92.5%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 11194830Cuprous 2-thiophenecarboxylate触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a mixture of benzo[d][1,3]dioxol-5-ylboronic acid (0.39 g, 2.30 mmol), ligand TFP (0.07 g, 0.3 mmol), Pd2dba3 (0.14 g, 0.16 mmol), copper (I) thiophene-2-carboxylate (0.45 g, 2.4 mmol) was added a solution of 4-phenylsulfanylcarbonyl-piperidine-1-carboxylic acid tert-butyl ester (0.5 g, 1.6 mmol) in 10 mL of THF while purging with N2 at 50° C. After 18 hours the reaction mixture was diluted with ethyl acetate, filtered through celite then concentrated in vacuo. Purification by flash chromatography gave the title compound (0.52 g, 1.48 mmol). MS (ESI) m/z 333.8 (M+H+); HPLC (Novapak 150×3.9 mm C-18 column: mobile phase: 35-90% acetonitrile/water with 0.1% TFA, at 2 mL/min over 2 min.) t 1.52 min.

後処理

  1. customwhile purging with N2 at 50° C
  2. additionAfter 18 hours the reaction mixture was diluted with ethyl acetate
  3. filtrationfiltered through celite
  4. concentrationthen concentrated in vacuo
  5. customPurification by flash chromatography

出典と根拠

ORDレコード
ord-c6eab6fe05664f54b7be1505481fadad
出典データセット
uspto-grants-2015_11
特許番号
US09181266B2

関連ノート

読み込み中…