Trimethyl orthoformate → {4-[(4-dipropylamino-butylamino)-methyl]-benzyl}-carbamic Acid t-butyl Ester

HRID 348718Notes

Reaction equation

HRID 348718 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]=O)=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:18]([N:21]([CH2:27][CH2:28][CH3:29])[CH2:22][CH2:23][CH2:24][CH2:25][NH2:26])[CH2:19][CH3:20].C(OC)(OC)OC.[BH4-].[Na+]>CO.O>[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][NH:26][CH2:25][CH2:24][CH2:23][CH2:22][N:21]([CH2:27][CH2:28][CH3:29])[CH2:18][CH2:19][CH3:20])=[CH:11][CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 9005Trimethyl orthoformateHCID 2794832tert-Butyl hydrogen ((4-formylphenyl)methyl)carbonimidateHCID 4311764Sodium borohydrideHCID 7138396N,N-dipropylbutane-1,4-diamine

Product 1

HCID 66941782{4-[(4-dipropylamino-butylamino)-methyl]-benzyl}-carbamic Acid t-butyl EsterYield 79.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

The compound (225.3 mg) obtained in Example 103-3 was dissolved in methanol (6.76 ml). Then, the solution was added with the compound (165.0 mg) obtained in Example 1-2 and trimethyl orthoformate (304.8 mg), followed by stirring at room temperature for 18 hours. Sodium borohydride (108.7 mg) was added to the solution under ice-cooling, followed by stirring at room temperature for 0.5 hours. The reaction solution was added with water and subjected to separation/extraction with chloroform. Then, the extract was washed with saturated saline solution and dried with anhydrous sodium sulfate, followed by concentration under reduced pressure. The residue was purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (297.6 mg) as a colorless oily substance.

Workup

  1. temperaturecooling
  2. stirringby stirring at room temperature for 0.5 hours
  3. extractionsubjected to separation/extraction with chloroform
  4. washThen, the extract was washed with saturated saline solution
  5. dry with materialdried with anhydrous sodium sulfate
  6. concentrationfollowed by concentration under reduced pressure
  7. customThe residue was purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-b0c60fc8ae274c659ebaab002b8736cf
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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