2,2-Dimethoxypropane → tert-butyl (4S)-4-(2-methoxy-2-oxo-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylate

HRID 1254362Notes

Reaction equation

HRID 1254362 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:15][OH:16])[CH2:10][C:11]([O:13][CH3:14])=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].CO[C:19](OC)([CH3:21])[CH3:20]>CC(C)=O.B(F)(F)F.CCOCC>[CH3:14][O:13][C:11](=[O:12])[CH2:10][C@H:9]1[CH2:15][O:16][C:19]([CH3:21])([CH3:20])[N:8]1[C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7]

Participants

5

Reactant 2

HCID 64952,2-DimethoxypropaneHCID 54573797Methyl (S)-3-(Boc-amino)-4-hydroxybutanoate

Product 1

HCID 10923729tert-butyl (4S)-4-(2-methoxy-2-oxo-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylateYield 92%

Reagents, catalysts & solvents 2

HCID 8000Boron trifluoride etherateCatalystHCID 180AcetoneSolvent

Procedure

To a solution of (S)-methyl 3-(tert-butoxycarbonylamino)-4-hydroxybutanoate (7.0 g, 30.0 mmol) in acetone (90 mL), there was added 2,2-dimethoxypropane (37 mL, 300 mmol) followed by BF3.Et2O (0.11 mL, 0.9 mmol). The resulting solution was stirred at rt overnight. Solvents were removed under vacuum, and the residue was redissolved in ether (100 mL), washed with sat'd NaHCO3 (20 mL). Upon concentrating under vacuum, the residue was purified by flash column chromatography to give (S)-tert-butyl 4-(2-methoxy-2-oxoethyl)-2,2-dimethyloxazolidine-3-carboxylate (7.51 g, 92%). MS m/z 296 (M+Na+).

Workup

  1. customSolvents were removed under vacuum
  2. dissolutionthe residue was redissolved in ether (100 mL)
  3. washwashed with sat'd NaHCO3 (20 mL)
  4. concentrationUpon concentrating under vacuum
  5. customthe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-6316ef4bf1f34b8c8565447ccd5f4e21
Source dataset
uspto-grants-2013_06
Patent number
US08455521B2

Reaction notes

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