Reaktion #160201

Reaktionsgleichung

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

2-methylpropan-2-ol

2-methylbut-2-ene

NaClO2

→

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

Ausbeute 100.0%

Lösungsmittel

THF

water

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Filtrationfiltered through celite
2. 2
   Einengenconcentrated in vacuo
3. 3
   SonstigeThe residue was partitioned between sat. aq. sodium bicarbonate (50 mL) and ethyl acetate (50 mL)
4. 4
   Extraktionthe aqueous layer was extracted further with ethyl acetate (3×50 mL)
5. 5
   Waschenwashed with sat. aq. sodium bicarbonate (50 mL)
6. 6
   Trocknendried over MgSO4
7. 7
   Einengenconcentrated in vacuo
8. 8
   Temperaturthe reaction mixture was cooled to 0° C
9. 9
   workup.STIRRINGthe reaction mixture was stirred for 30 minutes
10. 10
    TemperaturThe reaction mixture was warmed to room temperature
11. 11
    Extraktionextracted with ethyl acetate (4×50 mL)
12. 12
    Waschenthe combined organic layer was washed with brine (15 mL)
13. 13
    Trocknendried over MgSO4
14. 14
    Filtrationfiltered
15. 15
    Einengenconcentrated in vacuo

Vorschrift

To [8-benzyl-10-(1,2-dihydroxyethyl)-11-oxa-3,8-diazaspiro[5.5]undecan-3-yl]-(4-isopropoxy-3-methyl-phenyl)methanone (1.53 g, 3.17 mmol) in THF (28 mL) was added NaIO4 (1.36 g, 6.34 mmol) followed by the addition of water (10 mL). The reaction mixture was stirred at room temperature for 2 hours, then filtered through celite, and concentrated in vacuo. The residue was partitioned between sat. aq. sodium bicarbonate (50 mL) and ethyl acetate (50 mL) and 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, and concentrated in vacuo. To the intermediate aldehyde (˜1.4 g) was added 2-methylpropan-2-ol (17 mL) and 2-methylbut-2-ene (9 mL, 85.08 mmol) and the reaction mixture was cooled to 0° C. A solution of NaClO2 (938 mg, 8.29 mmol) and NaH2PO4 (1.15 g, 8.31 mmol) in water (17 mL) was added dropwise over 5 minutes, and the reaction mixture was stirred for 30 minutes. The reaction mixture was warmed to room temperature, then extracted with ethyl acetate (4×50 mL) and the combined organic layer was washed with brine (15 mL), dried over MgSO4, filtered and concentrated in vacuo to give 8-benzyl-3-(4-isopropoxy-3-methyl-benzoyl)-11-oxa-3,8-diazaspiro[5.5]undecane-10-carboxylic acid as a white foam (1.48 g, 100%). ESI-MS m/z calc. 466.6. Found 467.5 (M+1)+; Retention time: 1.27 minutes (3 min run).

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