Cyclohexene oxide → HCID 11515285, compound

HRID 1698390Notes

Reaction equation

HRID 1698390 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:6]12[O:12][CH:7]1[CH2:8][CH2:9][CH2:10][CH2:11]2>O>[N:1]1([C@H:6]2[CH2:11][CH2:10][CH2:9][CH2:8][C@@H:7]2[OH:12])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 9246Cyclohexene oxideHCID 31268Pyrrolidine

Product 1

HCID 11515285HCID 11515285, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Pyrrolidine (10.5 g, 148 mmol), cyclohexene oxide (15 mL, 148 mmol) and water (5 mL) were refluxed under nitrogen for 7 h. 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 (+).

Workup

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

Sources & evidence

ORD record
ord-868968150616444f838a6f05b12431fb
Source dataset
uspto-grants-2012_04
Patent number
US08163938B2

Reaction notes

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