Dimethyl Sulfoxide → 3-Methyl-5-(1-methyl-2(S)-pyrrolidinyl)isoxazole

HRID 1721084Notes

Reaction equation

HRID 1721084 reaction equation
[C:1]([N:11]1[CH2:17][CH2:16][CH2:15][C@H:12]1[CH2:13][OH:14])(OCC1C=CC=CC=1)=O.C([N:20]([CH2:23][CH3:24])CC)C.[CH3:25]S(C)=O>>[CH3:25][C:23]1[CH:24]=[C:13]([C@@H:12]2[CH2:15][CH2:16][CH2:17][N:11]2[CH3:1])[O:14][N:20]=1

Participants

4

Reactant 3

HCID 679Dimethyl Sulfoxide2×HCID 8471TriethylamineHCID 11096562Cbz-L-Prolinol

Product 1

HCID 1193803-Methyl-5-(1-methyl-2(S)-pyrrolidinyl)isoxazoleYield 70%

Procedure

To a stirred solution of N-Cbz-L-prolinol (5 g, 21.26 mmol, from steps 24b or 24c above) in 20 mL of anhydrous DMSO were added 8.89 mL (63.79 mmol) of triethylamine and 10.75 g (63.79 mmol) of SO3 -pyridine complex in 35 mL of DMSO. The reaction mixture was stirred at room temperature for 10 min, then poured into 200 mL of ice water. The mixture was extracted with ether, the extract was dried over Na2SO4 and concentrated to afford the title product, 3.058 g (70% yield).

Workup

  1. extractionThe mixture was extracted with ether
  2. dry with materialthe extract was dried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-1b51e5fa1f3d4de5b6fe17c1ed933dfb
Source dataset
uspto-grants-1996_04
Patent number
US05508418

Reaction notes

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