Reaktion #220118

Reaktionsgleichung

( 3 )

(2R,4R)-tert-butyl 4-(allyloxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

(R)-2-isopropylpent-4-enoic acid

LiOH

H2O2

→

desired product

(S)-2-((R)-3-isopropyl-2-oxopyrrolidin-1-yl)-4-phenylbutanoic acid

Lösungsmittel

THF

water

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe ice bath was removed
2. 2
   workup.WAITto continue for 1 h at rt
3. 3
   workup.ADDITIONA solution of sodium sulfite (3.63 g) was added
4. 4
   workup.STIRRINGthe reaction stirred for 10 min
5. 5
   workup.ADDITIONSaturated sodium carbonate solution was added
6. 6
   Extraktionthe reaction was extracted with methylene chloride
7. 7
   Extraktionextracted 3 times with diethyl ether
8. 8
   WaschenThe combined ether layers were washed with brine
9. 9
   Trocknendried over MgSO4
10. 10
    FiltrationThe extract was filtered
11. 11
    Einengenconcentrated in vacuo

Vorschrift

Step D (3): (R)-2-isopropylpent-4-enoic acid. To a solution of the compound of step D (2) (1.08 g, 3.59 mmol) in THF (14.4 mL) was added water (3.59 mL), and the mixture cooled to 0° C. A solution of LiOH (172.5 mg, 7.20 mmol) and 30% H2O2 (3.26 mL) in water (11.2 mL) was added, and the combined mixture stirred for 10 minutes at 0° C. The ice bath was removed, and the reaction was allowed to continue for 1 h at rt. A solution of sodium sulfite (3.63 g) was added, and the reaction stirred for 10 min. Saturated sodium carbonate solution was added, and the reaction was extracted with methylene chloride. The aqueous layer was acidified to pH 1 with 6 N HCl, and extracted 3 times with diethyl ether. The combined ether layers were washed with brine, and dried over MgSO4. The extract was filtered, and concentrated in vacuo to afford the desired product.

Quelle