Benzyl tert-butyl (3-azidopropane-1,2-diyl)biscarbamate → Benzyl tert-butyl (3-aminopropane-1,2-diyl)biscarbamate

HRID 1504846Notes

Reaction equation

HRID 1504846 reaction equation
[N:1]([CH2:4][CH:5]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])[CH2:6][NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[N+]=[N-]>CO.[Pd]>[NH2:1][CH2:4][CH:5]([NH:18][C:19](=[O:25])[O:20][C:21]([CH3:23])([CH3:22])[CH3:24])[CH2:6][NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 1

HCID 86731715Benzyl tert-butyl (3-azidopropane-1,2-diyl)biscarbamate

Product 1

HCID 86731716Benzyl tert-butyl (3-aminopropane-1,2-diyl)biscarbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of benzyl tert-butyl (3-azidopropane-1,2-diyl)biscarbamate (1.3 g, 5.4 mmol) in methanol (40 mL) was added palladium on carbon (0.13 g, 10% w/w). The mixture was stirred under a hydrogen atmosphere at room temperature. After 14 hours, the reaction mixture was filtered through CELITE, and the filtrate was concentrated under reduced pressure to give benzyl tert-butyl (3-aminopropane-1,2-diyl)biscarbamate. MS ESI calc'd. for C16H26N3O4 [M+H]+ 324. found 324. 1H NMR (400 MHz, CD3OD) 7.28-7.24 (m, 5H), 5.02 (s, 2H), 3.81-3.75 (m, 1H), 3.50-3.42 (m, 2H), 2.68-2.55 (m, 2H), 1.39 (s, 9H).

Workup

  1. filtrationthe reaction mixture was filtered through CELITE
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-043b5b0d3ca540d587da03c880a9415d
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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