Triethylamine → HCID 14347787, compound

HRID 2232084Notes

Reaction equation

HRID 2232084 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]([OH:13])[CH:10]([CH2:14]O)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25]>ClCCl>[CH2:1]([N:8]1[CH2:12][CH:11]([OH:13])[CH:10]([CH2:14][S:24]([CH3:23])(=[O:26])=[O:25])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 13959884HCID 13959884, compound

Product 1

HCID 14347787HCID 14347787, compoundYield 93.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-Benzyl-3-hydroxymethyl-4-hydroxypyrrolidine (66.2 g) and triethylamine (38.8 g) are added to dry dichloromethane (700 ml) and the mixture is cooled till a temperature of from -5° to -10° C. At this temperature, methanesulfonyl chloride (36.6 g) is added dropwise to the mixture with stirring. After the addition, the mixture is stirred for 30 minutes, and then washed with an aqueous sodium hydrogen carbonate and subsequently with water. Thereafter, the dichloromethane layer is separated, dried and concentrated to give 1-benzyl-4-hydroxy-3-methanesulfonylmethylpyrrolidine (80.8 g) as an oil.

Workup

  1. temperaturethe mixture is cooled till a temperature of from -5° to -10° C
  2. additionAfter the addition
  3. stirringthe mixture is stirred for 30 minutes
  4. washwashed with an aqueous sodium hydrogen carbonate and subsequently with water
  5. customThereafter, the dichloromethane layer is separated
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f89bde580a284ebcbd0dc7832418e65e
Source dataset
uspto-grants-1988_11
Patent number
US04786649

Reaction notes

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