Acetic Acid → 1-(4-Boc-aminobutyl)piperazine

HRID 1097298노트

반응식

HRID 1097298 반응식
C(OC([N:11]1[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:13][CH2:12]1)=O)C1C=CC=CC=1.C(O)(=O)C>CO.[OH-].[OH-].[Pd+2]>[C:25]([O:24][C:22](=[O:23])[NH:21][CH2:20][CH2:19][CH2:18][CH2:17][N:14]1[CH2:15][CH2:16][NH:11][CH2:12][CH2:13]1)([CH3:28])([CH3:26])[CH3:27]

참가 물질

5

반응물 2

HCID 176Acetic AcidHCID 59708788HCID 59708788, 화합물

생성물 1

HCID 41346911-(4-Boc-aminobutyl)piperazine수율 91%

시약·촉매·용매 2

HCID 9942167Palladium hydroxide촉매HCID 887Methanol용매

실험 절차

A mixture of 4-(4-tert-butoxycarbonylaminobutyl)piperazine-1-carboxylic acid benzyl ester (16) (3.26 g, 8.33 mmol), acetic acid (0.5 mL), and palladium hydroxide on carbon (60% wet, 0.98 g) in methanol (15 mL) was stirred under atmospheric hydrogen for 16 h. The catalyst was removed by suction filtration over Celite. The filtrate was concentrated in vacuo and the resulting residue was purified by Biotage silica gel column chromatography using concentrated ammonium hydroxide/methanol/dichloromethane to give 17 as a yellow oil (1.94 g, 91% yield): 1H NMR (300 MHz, CDCl3) δ 1.44 (s, 9H), 1.53 (m, 4H), 2.35 (m, 6H), 2.45 (br, 1H), 2.94 (t, 4H), 3.12 (m, 2H), 5.32 (br, 1H); ESI MS m/z 258 [C13H27N3O2+H]+.

후처리

  1. customThe catalyst was removed by suction filtration over Celite
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe resulting residue was purified by Biotage silica gel column chromatography

출처 및 근거

ORD 기록
ord-113925ec462a4b68b1396b0c3646ebc4
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143256B2

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