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

HRID 2080783Notes

Reaction equation

HRID 2080783 reaction equation
[CH2:1]([N:4]([CH2:10][CH2:11][CH3:12])[CH2:5][CH2:6][CH2:7][CH2:8][NH2:9])[CH2:2][CH3:3].C(OC)(OC)OC.[C:20]([O:24][C:25](=[O:36])[NH:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]([CH:34]=O)=[CH:30][CH:29]=1)([CH3:23])([CH3:22])[CH3:21].[BH4-].[Na+]>CO>[C:20]([O:24][C:25](=[O:36])[NH:26][CH2:27][C:28]1[CH:29]=[CH:30][C:31]([CH2:34][NH:9][CH2:8][CH2:7][CH2:6][CH2:5][N:4]([CH2:1][CH2:2][CH3:3])[CH2:10][CH2:11][CH3:12])=[CH:32][CH:33]=1)([CH3:23])([CH3:22])[CH3:21]

Participants

6

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 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (9.25 g) obtained in Example 1-2 was dissolved in anhydrous methanol (200 ml) and then added with trimethyl orthoformate (8.81 ml) and the compound (12.6 g) obtained in Example 23-3. The whole was stirred at room temperature for 1.5 hours under a nitrogen atmosphere. Then, sodium borohydride (2.03 g) was added thereto in an ice bath and the whole was stirred at room temperature for 2 hours. After completion of the reaction, distilled water was added thereto and the whole was stirred for a while. The solution was subjected to extraction with chloroform and washed with a saturated saline solution. The organic layer was dried with anhydrous sodium sulfate. The solvent was distilled off, thereby obtaining the subject compound (19.3 g) as a colorless oily substance.

Workup

  1. stirringin an ice bath and the whole was stirred at room temperature for 2 hours
  2. customAfter completion of the reaction
  3. distillationdistilled water
  4. additionwas added
  5. stirringthe whole was stirred for a while
  6. extractionThe solution was subjected to extraction with chloroform
  7. washwashed with a saturated saline solution
  8. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  9. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-d6cd9048e06d4584a2ef13311ab96745
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

Loading…