2,6-Lutidine → HCID 57947701, compound

HRID 416406Notes

Reaction equation

HRID 416406 reaction equation
C(O[C:6]([N:8](C)[C@H:9]([CH2:16][O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH2:10][CH2:11][C:12](OC)=[O:13])=O)(C)(C)C.N1C(C)=CC=CC=1C.[Si](OS(C(F)(F)F)(=O)=O)(C)(C)C>C(Cl)Cl>[Si:18]([O:17][CH2:16][C@@H:9]([NH:8][CH3:6])[CH2:10][CH2:11][CH2:12][OH:13])([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 65367Trimethylsilyl triflateHCID 57947505HCID 57947505, compound

Product 1

HCID 57947701HCID 57947701, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-methyl 4-(tert-butoxycarbonyl(methyl)amino)-5-(tert-butyldimethylsilyloxy)pentanoate (37.9 g, 109.2 mmol) in DCM (200 mL) was added 2,6-lutidine (25.3 mL, 218.4 mmol) followed by TMSOTf (29.6 mL, 163.8 mmol). The resulting solution was stirred at RT for 1 h. The solvent was removed and the remaining residue was diluted with EtOAc. The organic mixture was washed with water and brine, dried over Na2SO4, filtered, and concentrated to give (S)-5-(tert-butyldimethylsilyloxy)-4-(methylamino)pentan-1-ol, which was used without further purification. LRMS (M+H+) m/z 248.2.

Workup

  1. customThe solvent was removed
  2. additionthe remaining residue was diluted with EtOAc
  3. washThe organic mixture was washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-588931341ad849deafdea10b3b9926b8
Source dataset
uspto-grants-2012_01
Patent number
US08088793B2

Reaction notes

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