Dimethyl Sulfoxide → 2-(Pyrrolidin-1-yl)cyclohexanone

HRID 1598792Notes

Reaction equation

HRID 1598792 reaction equation
C(Cl)(=O)C(Cl)=O.C(Cl)Cl.CS(C)=O.[N:14]1([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH:20]2[OH:25])[CH2:18][CH2:17][CH2:16][CH2:15]1>CCN(CC)CC>[N:14]1([CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][C:20]2=[O:25])[CH2:15][CH2:16][CH2:17][CH2:18]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 119888572-(Pyrrolidin-1-yl)cyclohexan-1-ol

Product 1

HCID 126490752-(Pyrrolidin-1-yl)cyclohexanoneYield 72%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A solution of oxalyl chloride (50 mL, 0.5732 mol) in 200 mL of freshly distilled CH2Cl2 was cooled down to -70° C. and DMSO (80 mL, 1.1274 mol) was carefully added dropwise. After 15 min., 2-(1-pyrrolidinyl)cyclohexanol (a) (70 g, 0.4142 mol) was added to the reaction mixture, followed by Et3N (350 mL). The cold bath was then removed, and the mixture was stirred at room temperature for two and a half hours. Progress of the reaction was followed by gas chromatography. The solvent was partially removed in vacuo and ethyl ether (200 mL) was added. This organic layer was washed with brine (3×100 mL), dried (Na2SO4), and the solvent removed in vacuo. The crude product was distilled under high vacuum (BP: 84° C./0.5 mmHg) to yield 49.5 g of the ketone (b) as a colorless oil (72%). Rf : 0.49 (CHCl3 :MeOH:NH4OH=92:7:1); B.P: 84° C. (0.5 mmHg); IR (neat) 2940, 2860, 2800, 1715, 1440 cm-1 ; 1H-NMR (CDCl3) d 1.53-1.63 (m, 1H), 1.72 (m, 4H), 1.76-1.93 (m, 4H), 1.94-2.04 (m, 1H), 2.21, (m, 1H), 2.52 (m, 5H), 2.83 (dd, 1H, J1 =8.6, J2 =4.5 Hz); Mass Spectrum Calcd. for C10H17NO: 167.1310, Found: 167.1310.

Workup

  1. customThe cold bath was then removed
  2. customThe solvent was partially removed in vacuo and ethyl ether (200 mL)
  3. additionwas added
  4. washThis organic layer was washed with brine (3×100 mL)
  5. dry with materialdried (Na2SO4)
  6. customthe solvent removed in vacuo
  7. distillationThe crude product was distilled under high vacuum (BP: 84° C./0.5 mmHg)

Sources & evidence

ORD record
ord-d1a97ca2ea1b46ed9441a6b8fe3b4c6d
Source dataset
uspto-grants-1998_04
Patent number
US05739158

Reaction notes

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