Toluene → HCID 86649693, compound

HRID 37829Notes

Reaction equation

HRID 37829 reaction equation
[CH:1]1([C:6]2[CH:7]=[C:8]3[N:13]([CH:14]=2)[CH2:12][CH2:11][CH2:10][CH2:9]3)[CH2:5][CH2:4][CH2:3][CH2:2]1.C1(C)C=CC=CC=1.[C:22](Cl)(=[O:26])[C:23]([Cl:25])=[O:24]>C1COCC1>[CH:1]1([C:6]2[CH:7]=[C:8]3[N:13]([C:14]=2[C:22](=[O:26])[C:23]([Cl:25])=[O:24])[CH2:12][CH2:11][CH2:10][CH2:9]3)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 65578Oxalyl chlorideHCID 668510482-Cyclopentyl-5,6,7,8-tetrahydro-indolizine

Product 1

HCID 86649693HCID 86649693, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

2-Cyclopentyl-5,6,7,8-tetrahydro-indolizine (0.24 g, 1.27 mmol) was dissolved in THF (1 mL) and toluene (1.5 mL) and cooled to 0° C. Oxalyl chloride (0.14 mL, 1.52 mmol) was added dropwise and the mixture was stirred at 0° C. for 30 min, then at room temperature for 1 hour. Concentration in vacuo afforded (2-cyclopentyl-5,6,7,8-tetrahydro-indolizin-3-yl)-oxo-acetyl chloride (0.31 g, 88%) as a semi-solid.

Workup

  1. waitat room temperature for 1 hour
  2. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-d0991700f12c494e97606c7c2657724e
Source dataset
uspto-grants-2013_09
Patent number
US08524705B2

Reaction notes

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