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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
Notes
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Reaction equation

HRID 412561 reaction equation
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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-59828da760c042e884f41027733083ed
Source dataset
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06562828B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes