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

HRID 2039921Notes

Reaction equation

HRID 2039921 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-528caa24af7645f0b5fe280b789415a4
Source dataset
uspto-grants-2013_11
Patent number
US08580823B2

Reaction notes

Loading…