Water → benzyl N-[1-(azidomethyl)-3-methyl-butyl]carbamate
Reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH2:19][CH:20]([CH3:22])[CH3:21])[CH2:13]CS([O-])(=O)=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:23]=[N+:24]=[N-:25].[Na+].C(OCC)(=O)C.O>CN(C=O)C>[N:23]([CH2:13][CH:12]([NH:11][C:9](=[O:10])[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:19][CH:20]([CH3:22])[CH3:21])=[N+:24]=[N-:25]Participants
Procedure
To the crude [2-(benzyloxycarbonylamino)-4-methyl-pentyl]methanesulfonate from the above reaction in DMF (50 mL), was added sodium azide 2.43 g. The reaction mixture was then heated to 85 degrees for 3 hrs. After cooling, ethyl acetate (300 mL) and water was added. The organic layer was separated, dried with magnesium sulfate and then concentrated under vacuum to afford the crude benzyl N-[1-(azidomethyl)-3-methyl-butyl]carbamate. To this crude intermediate was added THF (100 mL) followed by triphenylphosphine 7.21 g and stirred under nitrogen for 16 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)-3-methyl-butyl]carbamate (4.5 g).
Workup
- temperatureThe reaction mixture was then heated to 85 degrees for 3 hrs
- temperatureAfter cooling
- customThe organic layer was separated
- dry with materialdried with magnesium sulfate
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-dcc890b9099d4a34971a86227e6ae33e
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08598197B2
Reaction notes
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