반응 #587232

반응 방정식

Pyrrolidine

cyclohexene oxide

→

(1S,2S)-2-(Pyrrolidinyl)cyclohexan-1-ol

수율 87.4%

용매

water

반응 조건

후처리

1. 1
   기타The cooled, orange mixture was partitioned between saturated sodium hydroxide aq (150 mL) and diethyl ether (150 mL)
2. 2
   세척The aqueous layer was back-washed with diethyl ether (75 ML)
3. 3
   건조the combined diethyl ether layers were dried over sodium sulfate
4. 4
   기타The diethyl ether was removed in vacuo the residual oil
5. 5
   workup.DISTILLATIONdistilled (bp 51° C. at full vacuum)

실험 절차

Pyrrolidine (10.5 g, 148 mmol), cyclohexene oxide (15 mL, 148 mmol) and water (5 mL) were refluxed under nitrogen for 7h. The cooled, orange mixture was partitioned between saturated sodium hydroxide aq (150 mL) and diethyl ether (150 mL). The aqueous layer was back-washed with diethyl ether (75 ML) and the combined diethyl ether layers were dried over sodium sulfate. The diethyl ether was removed in vacuo the residual oil was vacuum distilled (bp 51° C. at full vacuum) to give (1R,2R)/(1S,2S)-2-(Pyrrolidinyl)cyclohexan-1-ol (21.9 g, 87%). 13C NMR (50 MHz, APT, CDCl3) δ 70.47 (−), 64.82 (−), 47.44 (+), 33.15 (+), 25.11 (+), 24.23 (+), 24.00 (+), 21.12 (+).

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