Triethylamine → 1-(4-Aminophenyl)pyrrolidin-3-yl methanesulphonate

HRID 496521Notes

Reaction equation

HRID 496521 reaction equation
[S:1](Cl)([CH3:4])(=[O:3])=[O:2].[N+:6]([C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH2:19][CH2:18][CH:17]([OH:20])[CH2:16]2)=[CH:11][CH:10]=1)([O-])=O.C(N(CC)CC)C>C1COCC1>[CH3:4][S:1]([O:20][CH:17]1[CH2:18][CH2:19][N:15]([C:12]2[CH:13]=[CH:14][C:9]([NH2:6])=[CH:10][CH:11]=2)[CH2:16]1)(=[O:3])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 120678131-(4-Nitrophenyl)pyrrolidin-3-ol

Product 1

HCID 865904791-(4-Aminophenyl)pyrrolidin-3-yl methanesulphonateYield 106.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

40 ml (0.516 mol) of mesyl chloride was added dropwise at 5° C. to 83.3 g (0.4 mol) of N-(4-nitrophenly)-3-hydroxypyrrolidine (1) dissolved in 625 ml of anhydrous THF and 72.7 ml (0.6 mol) of triethylamine. The mixture was allowed to return to room temperature and was then poured onto ice. After filtering off the precipitate by suction and drying, 109 g of yellow powder (2) was obtained.

Workup

  1. customto return to room temperature
  2. additionwas then poured onto ice
  3. filtrationAfter filtering off the precipitate by suction
  4. customdrying

Sources & evidence

ORD record
ord-bc5ffff4fdec4db081d5df53b6e8b74e
Source dataset
uspto-grants-2005_09
Patent number
US06946005B2

Reaction notes

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