Triethylamine → 1-(4-Nitrophenyl)pyrrolid-3-yl methanesulphonate

HRID 719674Notes

Reaction equation

HRID 719674 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-:8])=[O:7].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:11]=[CH:10][C:9]([N+:6]([O-:8])=[O:7])=[CH:14][CH:13]=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 120678141-(4-Nitrophenyl)pyrrolid-3-yl methanesulphonate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

40 ml (0.516 mol) of mesyl chloride were added dropwise at 5° C. to 83.3 g (0.4 mol) of N-(4-nitrophenyl)-3-hydroxypyrrolidine 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 into ice to form a precipitate.

Workup

  1. customto return to room temperature
  2. additionwas then poured into ice
  3. customto form a precipitate

Sources & evidence

ORD record
ord-0de0dbf685c24b13abeb0f7d4f31d80e
Source dataset
uspto-grants-2006_11
Patent number
US07132534B2

Reaction notes

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