Water → HCID 69698031, compound

HRID 412564Notes

Reaction equation

HRID 412564 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]([N:18]1[CH2:27][CH2:26][C:25]2[C:20](=[CH:21][C:22]([O:28][CH2:29][CH:30]3[CH2:35][CH2:34][N:33]([CH2:36][C:37]([C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)=[O:38])[CH2:32][CH2:31]3)=[CH:23][CH:24]=2)[CH2:19]1)=[N:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].O>O1CCCC1.CO>[C:14]([O:13][C:11]([NH:10][C:9]([N:18]1[CH2:27][CH2:26][C:25]2[C:20](=[CH:21][C:22]([O:28][CH2:29][CH:30]3[CH2:31][CH2:32][N:33]([CH2:36][CH:37]([OH:38])[C:39]4[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=4)[CH2:34][CH2:35]3)=[CH:23][CH:24]=2)[CH2:19]1)=[N:8][C:6]([O:5][C:1]([CH3:3])([CH3:4])[CH3:2])=[O:7])=[O:12])([CH3:15])([CH3:16])[CH3:17]

Participants

6

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 69698211HCID 69698211, compound

Product 1

HCID 69698031HCID 69698031, compoundYield 74.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N,N′-di-tert-butoxycarbonyl-7-(1-phenacylpiperidin-4-ylmethoxy)-1,2,3,4-tetrahydroisoquinoline-2-carboxamidine (120 mg) in a mixture of tetrahydrofuran (1 ml) and methanol (0.2 ml) was added sodium borohydride (11 mg), and the mixture was stirred at room temperature for 2 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=5:1, 1% triethylamine) and dried under reduced pressure to give the title compound (90 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=5:1, 1% triethylamine)
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-dc2f91f1ce634ea4b3566f4acd1ab0af
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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