2,6-Lutidine → (S)-1-(tert-butyldimethylsilyloxy)-N-methylpent-4-en-2-amine

HRID 409821Notes

Reaction equation

HRID 409821 reaction equation
[Si:1]([O:8][CH2:9][C@@H:10]([N:14](C)[C:15](=O)OC(C)(C)C)[CH2:11][CH:12]=[CH2:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C(C)=CC=CC=1C.[Si](OS(C(F)(F)F)(=O)=O)(C)(C)C>C(Cl)Cl>[Si:1]([O:8][CH2:9][C@@H:10]([NH:14][CH3:15])[CH2:11][CH:12]=[CH2:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 65367Trimethylsilyl triflateHCID 57947449(S)-tert-butyl 1-(tert-butyldimethylsilyloxy)pent-4-en-2-yl(methyl)carbamate

Product 1

HCID 57947450(S)-1-(tert-butyldimethylsilyloxy)-N-methylpent-4-en-2-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)pent-4-en-2-yl(methyl)carbamate (10.5 g, 31.9 mmol) in DCM (100 mL) was added 2,6-lutidine (4.8 mL, 41.4 mmol) followed by TMSOTf (7.5 mL, 41.4 mmol). The resulting solution was stirred at RT for 30 min. The solvent was removed and the remaining residue was dried under vacuum to give (S)-1-(tert-butyldimethylsilyloxy)-N-methylpent-4-en-2-amine, which was used without further purification. LRMS (M+H+) m/z 230.2.

Workup

  1. customThe solvent was removed
  2. customthe remaining residue was dried under vacuum

Sources & evidence

ORD record
ord-30e2bc3b6ffb4273977d3e1cdd12afae
Source dataset
uspto-grants-2014_06
Patent number
US08759374B2

Reaction notes

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