Hydrochloric Acid → HCID 131718417, compound

HRID 1941585Notes

Reaction equation

HRID 1941585 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([O:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH2:10][C@H:9]1[CH2:18][OH:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33](Cl)(=[O:35])=[O:34])=[CH:29][CH:28]=1.Cl>ClCCl>[C:27]1([CH3:37])[CH:32]=[CH:31][C:30]([S:33]([O:19][CH2:18][C@@H:9]2[CH2:10][C@@H:11]([O:13][S:14]([CH3:17])(=[O:15])=[O:16])[CH2:12][N:8]2[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])(=[O:35])=[O:34])=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chloride2×HCID 8471Triethylamine2×HCID 10589967HCID 10589967, compound

Product 1

HCID 131718417HCID 131718417, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,4R)-1-t-butoxycarbonyl-4-methanesulfonyloxypyrrolidine-2-methanol (12.0 g) in dichloromethane (180 ml) stirring under ice cooling, triethylamine (6.23 ml), p-toluenesulfonyl chloride (8.52 g) and N,N-dimethylaminopyridine (993 mg) are successively added. The mixture is heated to reflux for 3 hours, supplemented with triethylamine (0.57 ml) and p-toluenesulfonyl chloride (775 mg), and heated to reflux for 1 hour. The reaction mixture is acidified with dilute hydrochloric acid. The organic layer is taken, washed with water, dried over sodium sulfate and concentrated in vacuo. The residue is purified by silica gel column chromatography and recrystallized from n-hexane to give (2S,4R)-1-t-butoxycarbonyl-4-methanesulfonyloxypyrrolidine-2-methanol p-toluenesulfonate (16.8 g). Yield: 92%. mp. 65° to 66° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for 3 hours
  3. temperatureheated
  4. temperatureto reflux for 1 hour
  5. washwashed with water
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by silica gel column chromatography
  9. customrecrystallized from n-hexane

Sources & evidence

ORD record
ord-f4e37413d2854c45a2cde8a3efbb9e2c
Source dataset
uspto-grants-1997_12
Patent number
US05703243

Reaction notes

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