Water → HCID 20254273, compound

HRID 1908196Notes

Reaction equation

HRID 1908196 reaction equation
[N:1]([CH2:4][CH:5]([NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:6]([CH3:8])[CH3:7])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.C(OCC)(=O)C>C1COCC1>[NH2:1][CH2:4][CH:5]([NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:6]([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 11776TriphenylphosphineHCID 85256537HCID 85256537, compound

Product 1

HCID 20254273HCID 20254273, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To benzyl N-[1-(azidomethyl)-2-methyl-propyl]carbamate 6.9 g (0.0263 mole) in THF (100 mL) was added triphenyl phosphine 7.59 g (1.1 eq). The contents were stirred for 20 hrs. After addition of water (10 mL), and stirring for an additional 6 hrs, ethyl acetate was added and the layers separated. After drying with magnesium sulfate and concentration under vacuum, the crude product was columned using DCM/MeOH (0-10%) to afford benzyl N-[1-(aminomethyl)-2-methyl-propyl]carbamate as a yellow oil.

Workup

  1. stirringstirring for an additional 6 hrs
  2. customthe layers separated
  3. dry with materialAfter drying with magnesium sulfate and concentration under vacuum

Sources & evidence

ORD record
ord-3d7643310b7248f0b2ab94d86a10e49e
Source dataset
uspto-grants-2013_12
Patent number
US08598197B2

Reaction notes

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