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Water → N,N'-Di-tert-butoxycarbonyl-7-[1-(2-hydroxyethyl)piperidin-4-ylmethoxy]-1,2,3,4-tetrahydroisoquinoline-2-carboxamidine

HRID 412561
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HRID 412561 반응식
C([O:3][C:4](=O)[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([CH2:12][O:13][C:14]2[CH:23]=[C:22]3[C:17]([CH2:18][CH2:19][N:20]([C:24](=[N:33][C:34]([O:36][C:37]([CH3:40])([CH3:39])[CH3:38])=[O:35])[NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:21]3)=[CH:16][CH:15]=2)[CH2:8][CH2:7]1)C.[BH4-].[Li+].O>O1CCCC1.CO>[C:37]([O:36][C:34]([NH:33][C:24]([N:20]1[CH2:19][CH2:18][C:17]2[C:22](=[CH:23][C:14]([O:13][CH2:12][CH:9]3[CH2:8][CH2:7][N:6]([CH2:5][CH2:4][OH:3])[CH2:11][CH2:10]3)=[CH:15][CH:16]=2)[CH2:21]1)=[N:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])=[O:35])([CH3:38])([CH3:39])[CH3:40]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 962WaterHCID 4148881Lithium borohydrideHCID 696966944-[2-(N,N'-Di-tert-butoxycarbonylamidino)-1,2,3,4-tetrahydroisoquinolin-7-yloxymethyl]piperidine-1-acetic acid ethyl ester

생성물 1

HCID 69696807N,N'-Di-tert-butoxycarbonyl-7-[1-(2-hydroxyethyl)piperidin-4-ylmethoxy]-1,2,3,4-tetrahydroisoquinoline-2-carboxamidine수율 45.2%

시약·촉매·용매 2

HCID 887
Methanol
용매
HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 4-[2-(N,N′-di-tert-butoxycarbonylamidino)-1,2,3,4-tetrahydroisoquinolin-7-yloxymethyl]piperidine-1-acetic acid ethyl ester (155 mg) in a mixture of tetrahydrofuran (2 ml) and methanol (0.008 ml) was added lithium borohydride (11 mg), and the mixture was stirred at room temperature for 3 hours. After completion of the reaction, water was added and the mixture was extracted with ethyl acetate and washed successively with water and saturated brine. The organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated. The obtained residue was purified by silica gel column chromatography (hexane:acetone=3:1) and dried under reduced pressure to give the title compound (65 mg).

후처리

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. washwashed successively with water and saturated brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated
  6. customThe obtained residue was purified by silica gel column chromatography (hexane:acetone=3:1)
  7. customdried under reduced pressure

출처 및 근거

ORD 기록
ord-59828da760c042e884f41027733083ed
출처 데이터셋
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06562828B1

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