Sodium cyanoborohydride → tert-butyl 4-(2,3-dihydro-1H-indol-7-yl)piperazine-1-carboxylate

HRID 1371518ノート

反応式

HRID 1371518 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:22]=2[NH:21][CH:20]=[CH:19]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([BH3-])#N.[Na+]>C(O)(=O)C.C(Cl)Cl.[OH-].[Na+]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:15]=[CH:16][CH:17]=[C:18]3[C:22]=2[NH:21][CH2:20][CH2:19]3)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

6

反応物 2

HCID 5003444Sodium cyanoborohydrideHCID 21070951tert-butyl 4-(1H-indol-7-yl)piperazine-1-carboxylate

生成物 1

HCID 21070950tert-butyl 4-(2,3-dihydro-1H-indol-7-yl)piperazine-1-carboxylate収率 46%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 6344Dichloromethane溶媒HCID 14798Sodium Hydroxide溶媒

実験手順

7-(4-t-Butyloxycarbonylpiperazin-1-yl)indole (200 mg, 0.67 mmol) is dissolved in acetic acid (4 mL). To the solution, sodium cyanoborohydride (84 mg, 1.33 mmol) is added. The reaction mixture is stirred for about 2 hours at r.t. The mixture is then diluted with DCM and NaOH (1M) is added. The organic layer is separated, dried and concentrated. The residue is chromatographed on the silica gel and the product containing fractions are combined to give about 93 mg of the 7-(4-t-butyloxycarbonylpiperazin-1-yl)-2,3-dihydroindole (46%).

後処理

  1. additionis added
  2. customThe organic layer is separated
  3. customdried
  4. concentrationconcentrated
  5. customThe residue is chromatographed on the silica gel
  6. additionthe product containing fractions

出典と根拠

ORDレコード
ord-d0406b2b6c834bf7a4c9eaf99970312d
出典データセット
uspto-grants-2007_01
特許番号
US07157463B2

反応ノート

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