Sodium cyanoborohydride → 1,13-Bisbenzyloxy-5,9-bisbenzyloxymethyl-4,7,10-triazatridecane

HRID 1733776Notes

Reaction equation

HRID 1733776 reaction equation
N[CH:2]([CH2:17][O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH2:3][NH:4][CH2:5][CH:6]([NH2:16])[CH2:7][O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[CH2:26]([O:33][CH2:34][CH2:35][CH:36]=O)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[C:38]([BH3-])#[N:39].[Na+]>CO>[CH2:26]([O:33][CH2:34][CH2:35][CH2:36][NH:16][CH:6]([CH2:7][O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[CH2:5][NH:4][CH2:3][CH:2]([CH2:17][O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[NH:39][CH2:38][CH2:6][CH2:7][O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 108882613-(Benzyloxy)propanalHCID 194385191,5-Diamino-1,5-dibenzyloxymethyl-3-azapentane

Product 1

HCID 194385051,13-Bisbenzyloxy-5,9-bisbenzyloxymethyl-4,7,10-triazatridecane

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1,5-Diamino-1,5-dibenzyloxymethyl-3-azapentane (0.50 g, 1.5 mmol) was dissolved in methanol (20 ml). 3-Benzyloxypropanal (0.50 q, 3 mmol), sodium cyanoborohydride (0.11 g, 3 mmol) and 3 Å molecular sieve (10 g) were added and the mixture was stirred for 16 hours at ambient temperature. The reaction mixture was filtered, water (20 ml) was added and the mixture was acidified with hydrochloric acid to pH 3. The mixture was extracted with diethyl ether (2-25 ml), the ether solution was dried with magnesium sulphate, the solution was evaporated and the mixture was chromatographed on silica. 1,13-Bisbenzyloxy-5,9-bisbenzyloxymethyl-4,7,10-triazatridecane was isolated as a white solid. Yield 0.40 g (42%), FAB MS: 640(M+1). The structure was confirmed by 1H NMR and 13C NMR.

Workup

  1. filtrationThe reaction mixture was filtered
  2. additionwater (20 ml) was added
  3. extractionThe mixture was extracted with diethyl ether (2-25 ml)
  4. dry with materialthe ether solution was dried with magnesium sulphate
  5. customthe solution was evaporated
  6. customthe mixture was chromatographed on silica

Sources & evidence

ORD record
ord-908be90dd3d2488ebae654e2a2516e88
Source dataset
uspto-grants-1996_07
Patent number
US05531978

Reaction notes

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