p-Toluenesulfonic acid monohydrate → (3S)-3-Fluoropyrrolidine 4-methylbenzenesulfonate

HRID 494300Notes

Reaction equation

HRID 494300 reaction equation
O.[CH3:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([OH:12])(=[O:11])=[O:10])=[CH:5][CH:4]=1.C([N:20]1[CH2:24][CH2:23][C@H:22]([F:25])[CH2:21]1)(OC(C)(C)C)=O>C(#N)C>[CH3:2][C:3]1[CH:4]=[CH:5][C:6]([S:9]([OH:12])(=[O:11])=[O:10])=[CH:7][CH:8]=1.[F:25][C@H:22]1[CH2:23][CH2:24][NH:20][CH2:21]1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 18453464tert-Butyl (3S)-3-fluoropyrrolidine-1-carboxylate

Product 1

HCID 86614633(3S)-3-Fluoropyrrolidine 4-methylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-Methylbenzenesulfonic acid monohydrate (752 mg, 3.95 mmol) was added to a stirred solution of Step 2 intermediate (280 mg, 1.48 mmol) in dry acetonitrile (20 ml) and the mixture was stirred at room temperature for 24 h under nitrogen atmosphere. The solvent was evaporated under reduced pressure and the oily residue obtained was triturated with dry diethyl ether (10 ml) to give 563 mg of the product as a white crystalline solid, which was used as such for the next step; IR (neat) 3443, 3019, 2783, 1626, 1434, 1215, 1034 cm−1

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe oily residue obtained
  3. customwas triturated with dry diethyl ether (10 ml)

Sources & evidence

ORD record
ord-a5d751681e0c4ae9808204ba7622b34a
Source dataset
uspto-grants-2009_05
Patent number
US07538128B2

Reaction notes

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