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

HRID 1371518노트

반응식

HRID 1371518 반응식
[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]

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 6344Dichloromethane용매HCID 14798Sodium Hydroxide용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-d0406b2b6c834bf7a4c9eaf99970312d
출처 데이터셋
uspto-grants-2007_01
특허 번호
US07157463B2

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