Triethylamine → (4-fluorophenyl)-[(2S)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanone

HRID 1676944Notes

Reaction equation

HRID 1676944 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C@H:2]1[CH2:6][N:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1.C(N(CC)CC)C.[F:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1>ClCCl>[F:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]([N:1]2[CH2:5][CH2:4][CH2:3][C@H:2]2[CH2:6][N:7]2[CH2:11][CH2:10][CH2:9][CH2:8]2)=[O:25])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 678794-Fluorobenzoyl chlorideHCID 853152(S)-(+)-1-(2-Pyrrolidinylmethyl)pyrrolidine

Product 1

HCID 11965126(4-fluorophenyl)-[(2S)-2-(pyrrolidin-1-ylmethyl)pyrrolidin-1-yl]methanoneYield 83.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

(S)(+)-1-(2-Pyrrolidinylmethyl)pyrrolidine (1.07 g, 6.93 mmol) and triethylamine (763 mg, 7.56 mmol) are dissolved in dichloromethane (20 mL) and cooled to 0° C. 4-Fluorobenzoyl chloride (1.00 g, 6.3 mmol) in dichloromethane (2 mL) is added to the mixture at 0° C. and stirred at room temperature for 3 h. The reaction mixture is washed with brine, dried over Na2SO4, and evaporated. The residue is purified by silica-gel column chromatography (CH2Cl2:2M NH3 in MeOH=40:1) to give 1.45 g (83%) of the title compound. MS (APCI+) 277(M+1)+.

Workup

  1. washThe reaction mixture is washed with brine
  2. dry with materialdried over Na2SO4
  3. customevaporated
  4. customThe residue is purified by silica-gel column chromatography (CH2Cl2:2M NH3 in MeOH=40:1)

Sources & evidence

ORD record
ord-9fc812d3804443fda062af551f6edb05
Source dataset
uspto-grants-2011_08
Patent number
US08008296B2

Reaction notes

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