Triethylamine → 3-Fluoro-3-(1-methanesulfonyloxyethyl)pyrrolidine-1-carboxylic acid benzyl ester

HRID 729439Notes

Reaction equation

HRID 729439 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C:13]([F:19])([CH:16]([OH:18])[CH3:17])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:27][S:28](Cl)(=[O:30])=[O:29]>ClCCl>[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH2:14][C:13]([F:19])([CH:16]([O:18][S:28]([CH3:27])(=[O:30])=[O:29])[CH3:17])[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 690767793-Fluoro-3-(1-hydroxyethyl)pyrrolidine-1-carboxylic acid benzyl ester

Product 1

HCID 866071353-Fluoro-3-(1-methanesulfonyloxyethyl)pyrrolidine-1-carboxylic acid benzyl esterYield 95.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a −10° C. solution of 3-fluoro-3-(1-hydroxyethyl)pyrrolidine-1-carboxylic acid benzyl ester (Example A14, 0.267 g, 1.00 mmol), triethylamine (0.4 g, 4 mmol) and dichloromethane (10 mL) is added methanesulfonyl chloride (0.229 g, 2.00 mmol). The mixture is stirred at room temperature for 2 hours and concentrated in vacuo. The residue is partitioned between ethyl acetate and water. The organic layer is dried over Na2SO4 and concentrated to afford the title compound (0.330 g). 1H NMR (200 MHz, CDCl3): δ 7.36 (s, 5H), 5.14 (s, 2H), 4.99-4.81 (m, 1H), 3.76-3.37 (m, 4H), 3.06 (s, 3H), 2.25-1.96 (m, 2H), 1.52-1.47 (m, 3H).

Workup

  1. customTo a −10° C.
  2. concentrationconcentrated in vacuo
  3. customThe residue is partitioned between ethyl acetate and water
  4. dry with materialThe organic layer is dried over Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-b434e81f0287449cb82506b2cb5901f5
Source dataset
uspto-grants-2009_09
Patent number
US07582627B2

Reaction notes

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