Triethylamine → 1-Benzylpyrrolidin-3-yl methanesulfonate

HRID 16243

Reaction equation

HRID 16243 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-6aba10ad0d9e4fbfb043799c04450e0e
Source dataset
uspto-grants-2010_06
Patent number
US07737159B2

Linked notes

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