Triethylamine → 1-Benzyl-3-hydroxy-4-methanesulfonyloxymethylpyrrolidine

HRID 649141Notes

Reaction equation

HRID 649141 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]([CH2:13][OH:14])[CH:10]([OH:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:16][S:17](Cl)(=[O:19])=[O:18].C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH2:1]([N:8]1[CH2:12][CH:11]([CH2:13][O:14][S:17]([CH3:16])(=[O:19])=[O:18])[CH:10]([OH:15])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 13959884HCID 13959884, compound

Product 1

HCID 201424581-Benzyl-3-hydroxy-4-methanesulfonyloxymethylpyrrolidineYield 53.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The known compound, 1-benzyl-3-hydroxy-4-hydroxymethylpyrrolidine [see J. Org. Chem., 30, 740 (1965)] (110 g) was allowed to react in chloroform with methanesulfonyl chloride (60.9 g) in the presence of triethylamine to yield 1-benzyl-3-hydroxy-4-methanesulfonyloxymethylpyrrolidine (81 g) as an oil.

Sources & evidence

ORD record
ord-e6960d2e7236433fad475648ad77d1c2
Source dataset
uspto-grants-1988_04
Patent number
US04738968

Reaction notes

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