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

HRID 451868Notes

Reaction equation

HRID 451868 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].CCN(CC)CC>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

6

Reactant 3

HCID 83002-MethoxypropeneHCID 8471TriethylamineHCID 11107667(S)-methyl 4-(tert-butoxycarbonylamino)-5-hydroxypentanoate

Product 1

HCID 15930243Methyl (S)-3-Boc-2,2-dimethyloxazolidine-4-propanoateYield 72%

Reagents, catalysts & solvents 2

HCID 8000Boron trifluoride etherateCatalystHCID 180AcetoneSolvent

Procedure

(S)-methyl 4-(tert-butoxycarbonylamino)-5-hydroxypentanoate (12 g, 48.6 mmol) and isopropenyl methyl ether (44.4 g, 427.3 mmol) was dissolved in acetone (200 mL) and BF3.Et2O (0.41 mL, 2.92 mmol) was added at rt and stirred for 1 hour. The reaction was stopped by addition of Et3N (5.8 mL). The reaction solution was washed with 100 mL of saturated NaHCO3 and evaporated, and (S)-tert-butyl 4-(3-methoxy-3-oxopropyl)-2,2-dimethyloxazolidine-3-carboxylate (10 g, yield 72%) was obtained as an oil that was used in the next step without further purification.

Workup

  1. washThe reaction solution was washed with 100 mL of saturated NaHCO3
  2. customevaporated

Sources & evidence

ORD record
ord-9bdc6161648b4494bdcfd473b529df82
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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