반응 #1482114

반응 방정식

NaOH

H2O2

20-4

tert-Butyl 2-methyl-2-phenyl-2,5-dihydro-1H-pyrrole-1-carboxylate

Water

→

tert-butyl 4-hydroxy-2-methyl-2-phenylpyrrolidine-1-carboxylate

용매

THF

THF

반응 조건

후처리

1. 1
   기타at 25° C
2. 2
   기타The reaction was partitioned between sat. aq. NaHCO3 (100 mL) and EtOAc (2×100 mL)
3. 3
   건조The combined organic layers were dried over Na2SO4
4. 4
   여과filtered
5. 5
   농축concentrated under reduced pressure
6. 6
   기타The residue was purified by flash column (SiO2

실험 절차

A solution of 20-4 (0.50 g, 1.9 mmol) in anhydrous THF (80 mL) at 0° C. was treated with BH3:THF (1.93 mL, 1.9 mmol) then stirred for 1 hour. at 25° C. Water (0.35 mL, 19.2 mmol) was added, followed by 3 N NaOH (0.23 mL, 5.8 mmol). The resulting solution was cooled to 0° C. prior to the addition of 30% H2O2 (0.22 mL, 1.9 mmol). The reaction was partitioned between sat. aq. NaHCO3 (100 mL) and EtOAc (2×100 mL). The combined organic layers were dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by flash column (SiO2, O-100% EtOAc/Hexanes gradient) to yield tert-butyl 4-hydroxy-2-methyl-2-phenylpyrrolidine-1-carboxylate, 20-5: LRMS m/z (M+H) 278.2 found, 278.1 required.

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