2-Methoxypropene → Methyl (S)-3-Boc-2,2-dimethyloxazolidine-4-propanoate

HRID 218406Notes

Reaction equation

HRID 218406 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:16][OH:17])[CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].CO[C:20]([CH3:22])=[CH2:21]>CC(C)=O.B(F)(F)F.CCOCC>[CH3:15][O:14][C:12](=[O:13])[CH2:11][CH2:10][C@H:9]1[CH2:16][O:17][C:20]([CH3:22])([CH3:21])[N:8]1[C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7]

Participants

5

Reactant 2

HCID 83002-MethoxypropeneHCID 11107667(S)-methyl 4-(tert-butoxycarbonylamino)-5-hydroxypentanoate

Product 1

HCID 15930243Methyl (S)-3-Boc-2,2-dimethyloxazolidine-4-propanoateYield 90%

Reagents, catalysts & solvents 2

HCID 8000Boron trifluoride etherateCatalystHCID 180AcetoneSolvent

Procedure

(S)-methyl 4-(tert-butoxycarbonylamino)-5-hydroxypentanoate (24 g, 97.2 mmol) and isopropenyl methyl ether (88.8 g, 854.6 mmol) was dissolved in acetone (2000 mL) and BF3-Et2O (0.82 mL, 5.84 mmol) was added at rt. The mixture was stirred for 1 hr at rt. The reaction was quenched by addition of Et3N (11.6 mL). The reaction solution was washed with aqueous saturated NaHCO3 (200 mL) and evaporated, and (S)-tert-butyl 4-(3-methoxy-3-oxopropyl)-2,2-dimethyloxazolidine-3-carboxylate (25.1 g, 90%) was obtained as an oil, which was used in the next step without further purification.

Workup

  1. customThe reaction was quenched by addition of Et3N (11.6 mL)
  2. washThe reaction solution was washed with aqueous saturated NaHCO3 (200 mL)
  3. customevaporated

Sources & evidence

ORD record
ord-c44805062cf641a794ff581b4940c4c3
Source dataset
uspto-grants-2012_06
Patent number
US08198453B2

Reaction notes

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