Diethyl Ether → HCID 20648582, compound

HRID 325246Notes

Reaction equation

HRID 325246 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][OH:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:22]1([S:28](Cl)(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(OCC)C>C(Cl)Cl.O>[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][S:28]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)(=[O:30])=[O:29])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 3283Diethyl EtherHCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 643448(S)-(-)-N-Boc-prolinol

Product 1

HCID 20648582HCID 20648582, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of N-t-Butoxycarbonyl-2(S)-hydroxymethylpyrrolidine (2.01 g, 10.00 mmol) and triethyl amine (1.70 mL, 12.00 mmol) in 10 mL of methylene chloride was cooled in an ice bath and treated with benzenesulfonylchloride (1.96 g, 11.00 mmol) and the mixture placed in a refridgerator overnight. The mixture was allowed to reach room temperaure and partioned between ethyl ether and water. The aqueous phase was extracted with ether and the combined organic layers washed with water 1N HCl, saturated sodium bicarbonate, brine, dried, filtered and concentrated. The residue was purified by column chromatography on silica gel (120 g, 25% ethyl acetate/hexanes) to provide 2.82 g (83%) of the title compound. MS (DCI, NH3): 359 (M+NH4)+.

Workup

  1. extractionThe aqueous phase was extracted with ether
  2. washthe combined organic layers washed with water 1N HCl, saturated sodium bicarbonate, brine
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by column chromatography on silica gel (120 g, 25% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-0dbbf063939a4d7f83e9ea9aed9c236d
Source dataset
uspto-grants-2001_04
Patent number
US06221865B1

Reaction notes

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