Benzyl tert-butyl [3-(acetylamino)propane-1,2-diyl]biscarbamate → Tert-butyl [1-(acetylamino)-3-aminopropan-2-yl]carbamate

HRID 1504848Notes

Reaction equation

HRID 1504848 reaction equation
[C:1]([NH:4][CH2:5][CH:6]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:7][NH:8]C(=O)OCC1C=CC=CC=1)(=[O:3])[CH3:2]>CO.[Pd]>[C:1]([NH:4][CH2:5][CH:6]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:7][NH2:8])(=[O:3])[CH3:2]

Participants

4

Reactant 1

HCID 86731717Benzyl tert-butyl [3-(acetylamino)propane-1,2-diyl]biscarbamate

Product 1

HCID 86731718Tert-butyl [1-(acetylamino)-3-aminopropan-2-yl]carbamate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of benzyl tert-butyl [3-(acetylamino)propane-1,2-diyl]biscarbamate (1.3 g, 3.6 mmol) in methanol (40 mL) was added 10% palladium on carbon (0.13 g, 10% w/w). The reaction mixture was stirred under a hydrogen atmosphere at room temperature. After 14 hours, the reaction mixture was filtered, and the filtrate was concentrated under reduced pressure to give tert-butyl [1-(acetylamino)-3-aminopropan-2-yl]carbamate. MS ESI calc'd. for C10H22N3O3 [M+H]+ 232. found 232. 1H NMR (400 MHz, CD3OD) δ 3.78-3.73 (m, 1H), 3.29-3.24 (m, 2H), 2.89-2.70 (m, 2H), 1.96 (s, 3H), 1.45 (s, 9H).

Workup

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

Sources & evidence

ORD record
ord-dc0e716a9dc3446ca2bea6b8664a30e1
Source dataset
uspto-grants-2015_12
Patent number
US09216173B2

Reaction notes

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