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

HRID 37043Notes

Reaction equation

HRID 37043 reaction equation
NC(COCC1C=CC=CC=1)CNCC(N)COCC1C=CC=CC=1.[CH2:26]([O:33][CH2:34][CH2:35][CH2:36][NH:37][CH:38]([CH2:64][O:65][CH2:66][C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1)[CH2:39][NH:40][CH2:41][CH:42]([CH2:55][O:56][CH2:57][C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)[NH:43][CH2:44][CH2:45][CH2:46][O:47][CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(OCCC=O)C1C=CC=CC=1.C([BH3-])#N.[Na+]>CO>[CH2:26]([O:33][CH2:34][CH2:35][CH2:36][NH:37][CH:38]([CH2:64][O:65][CH2:66][C:67]1[CH:68]=[CH:69][CH:70]=[CH:71][CH:72]=1)[CH2:39][NH:40][CH2:41][CH:42]([CH2:55][O:56][CH2:57][C:58]1[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=1)[NH:43][CH2:44][CH2:45][CH2:46][O:47][CH2:48][C:49]1[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 108882613-(Benzyloxy)propanalHCID 867486841,13-Bisbenzyloxy-5,9-bisbenzyloxymethyl-4,7,10-triazatridecane 1,5-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

1,13-Bisbenzyloxy-5,9-bisbenzyloxymethyl-4,7,10-triazatridecane 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-2369ec2926a24e8ebc8b3a6458ffae7e
Source dataset
uspto-grants-1995_05
Patent number
US05419893

Reaction notes

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