Chloroacetyl chloride → 2-Chloro-1-[(3s)-3-fluoropyrrolidin-1-yl]-1-ethanone

HRID 494301Notes

Reaction equation

HRID 494301 reaction equation
CC1C=CC(S(O)(=O)=O)=CC=1.[F:12][C@H:13]1[CH2:17][CH2:16][NH:15][CH2:14]1.C(N(CC)CC)C.[Cl:25][CH2:26][C:27](Cl)=[O:28]>ClCCl.O>[Cl:25][CH2:26][C:27]([N:15]1[CH2:16][CH2:17][C@H:13]([F:12])[CH2:14]1)=[O:28]

Participants

6

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 86614633(3S)-3-Fluoropyrrolidine 4-methylbenzenesulfonate

Product 1

HCID 552981152-Chloro-1-[(3s)-3-fluoropyrrolidin-1-yl]-1-ethanone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of Step 3 intermediate (563 mg, 1.48 mmol) and triethylamine (196 mg, 1.93 mmol) in dry dichloromethane (20 ml) was added drop wise (10 min) to a stirred and cooled (0° C.) solution of chloroacetyl chloride (186 mg, 1.63 mmol) in dry dichloromethane (5 ml) over 20 min. The resulting mixture was stirred at 0° C. for 2 h and diluted with water (50 ml). The organic layer was separated, washed with water (2×50 ml), brine and dried (Na2SO4). The solvent was evaporated under reduced pressure to give 124 mg of the desired compound as an off white solid; 1H NMR (CDCl3, 300 MHz) δ 1.35 (brs, 2H), 1.20-2.41 (m, 2H), 3.52-4.11 (m, 4H), 5.19-5.43 (m, 1H).

Workup

  1. stirringThe resulting mixture was stirred at 0° C. for 2 h
  2. customThe organic layer was separated
  3. washwashed with water (2×50 ml), brine
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-a31e18237f9d45fda340fc52de336214
Source dataset
uspto-grants-2009_05
Patent number
US07538128B2

Reaction notes

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