Magnesium trifluoromethanesulfonate → (S)-Methyl 3-((S)-1-(tert-butyldimethylsilyloxy)propan-2-yloxy)-2-hydroxypropanoate

HRID 1098218Notes

Reaction equation

HRID 1098218 reaction equation
FC(F)(F)S([O-])(=O)=O.[Mg+2].FC(F)(F)S([O-])(=O)=O.[O:18]1[CH2:20][C@H:19]1[C:21]([O:23][CH3:24])=[O:22].[Si:25]([O:32][CH2:33][C@@H:34]([OH:36])[CH3:35])([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]>CCOC(C)=O>[Si:25]([O:32][CH2:33][C@@H:34]([O:36][CH2:20][C@H:19]([OH:18])[C:21]([O:23][CH3:24])=[O:22])[CH3:35])([C:28]([CH3:31])([CH3:30])[CH3:29])([CH3:27])[CH3:26]

Participants

5

Reactant 3

HCID 2734125Magnesium trifluoromethanesulfonateHCID 10942355Methyl (2S)-2-oxiranecarboxylateHCID 13175136(S)-1-((Tert-butyldimethylsilyl)oxy)propan-2-OL

Product 1

HCID 86640846(S)-Methyl 3-((S)-1-(tert-butyldimethylsilyloxy)propan-2-yloxy)-2-hydroxypropanoateYield 37.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
10 °C

Procedure

Magnesium trifluoromethanesulfonate (0.974 g, 3.02 mmol) was added in one portion to (S)-methyl oxirane-2-carboxylate (1.234 g, 12.08 mmol) and (S)-1-(tert-butyldimethylsilyloxy)propan-2-ol (CAS no. 113534-13-7) (2.30 g, 12.08 mmol) in EtOAc (5 mL) cooled to 10° C. The resulting suspension was stirred at 10° C. for 10 minutes and then warmed to 45° C. and stirred for 2 days. The crude product was purified by flash silica chromatography, eluting with 0 to 30% EtOAc in isohexane to afford the product (1.336 g, 37.8%). 1H NMR (400 MHz, DMSO) δ0.00 (s, 6H), 0.83 (s, 9H), 0.98 (d, 3H), 3.34-3.53 (m, 3H), 3.55-3.64 (m, 5H), 4.11 (q, 1H), 5.39 (d, 1H)

Workup

  1. temperaturewarmed to 45° C.
  2. stirringstirred for 2 days
  3. customThe crude product was purified by flash silica chromatography
  4. washeluting with 0 to 30% EtOAc in isohexane

Sources & evidence

ORD record
ord-def69126da904439adb9a57acd51ca11
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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