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

HRID 451961Notes

Reaction equation

HRID 451961 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-87048e415588421092eca176b098f4d4
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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