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

HRID 340959Notes

Reaction equation

HRID 340959 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-5aed45551eef44ba9b3414ceaf7aa8a9
Source dataset
uspto-grants-2014_11
Patent number
US08895582B2

Reaction notes

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