Réaction #160205

Équation de réaction

[8-benzyl-10-(1,2-dihydroxyethyl)-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl]-(4-isopropoxy-3-methyl-phenyl)methanone

H2O

→

8-benzyl-3-(4-isopropoxy-3-methyl-benzoyl)-11-oxa-3,8-diazaspiro[5.5]undecane-10-carbaldehyde

Rendement 99.1%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   FiltrationThe reaction mixture was filtered
2. 2
   Autrepartitioned between sat. aq. sodium bicarbonate/ethyl acetate
3. 3
   ExtractionThe aqueous layer was extracted further with ethyl acetate (3×50 mL)
4. 4
   Lavagewashed with sat. aq. sodium bicarbonate (50 mL)
5. 5
   Séchagedried over MgSO4
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated in vacuo

Mode opératoire

To a solution of [8-benzyl-10-(1,2-dihydroxyethyl)-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl]-(4-isopropoxy-3-methyl-phenyl)methanone (417 mg, 0.86 mmol) in THF (10 mL) was added NaIO4 (468 mg, 2.19 mmol) and H2O (4 mL). The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was filtered and partitioned between sat. aq. sodium bicarbonate/ethyl acetate. The aqueous layer was extracted further with ethyl acetate (3×50 mL). The organics were combined, washed with sat. aq. sodium bicarbonate (50 mL), dried over MgSO4, filtered and concentrated in vacuo to yield 8-benzyl-3-(4-isopropoxy-3-methyl-benzoyl)-11-oxa-3,8-diazaspiro[5.5]undecane-10-carbaldehyde (384 mg, 99%) as a white solid. ESI-MS m/z calc. 450.3. Found 451.3 (M+1)+; Retention time: 1.33 minutes (3 min run).

Source