Triethylamine → 1-Benzylpyrrolidin-3-yl methanesulfonate

HRID 460436Notes

Reaction equation

HRID 460436 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][CH:10]([OH:13])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C1(C)C=CC=CC=1>[CH3:21][S:22]([O:13][CH:10]1[CH2:11][CH2:12][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:9]1)(=[O:24])=[O:23]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 69889N-benzyl-3-pyrrolidinol

Product 1

HCID 98998111-Benzylpyrrolidin-3-yl methanesulfonate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-Benzyl-3-pyrrolidinol (1.1 g) in toluene (10 mL) at 0° C. was treated with triethylamine (1 mL) and methanesulfonyl chloride (0.53 mL), warmed to room temperature, washed with saturated aqueous sodium bicarbonate, water, and brine, dried over anhydrous sodium sulfate, and concentrated. 1H NMR (300 MHz, DMSO-d6) δ 7.31 (s, 5H), 5.21 (m, 1H), 3.65 (q, 2H), 2.82 (m, 2H), 2.5 (m, 2H), 2.36 (m, 2H), 2.1 (m, 1H).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate, water, and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-38c0f84adeab4c0ebe34fcccd3b0c415
Source dataset
uspto-grants-2007_03
Patent number
US07196200B2

Reaction notes

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