Pyrrolidine → HCID 10109292, compound

HRID 966524Notes

Reaction equation

HRID 966524 reaction equation
[CH2:1]([O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH2:20][CH2:21]OS(C)(=O)=O)[CH:18]=2)[NH:13][C:12]=1[CH3:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1>O1CCOCC1>[CH2:1]([O:8][C:9]([C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH2:20][CH2:21][N:28]3[CH2:32][CH2:31][CH2:30][CH2:29]3)[CH:18]=2)[NH:13][C:12]=1[CH3:27])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 233938525-(2-Methanesulfonyloxy-ethyl)-2-methyl-1H-indole-3-carboxylic Acid Benzyl Ester

Product 1

HCID 10109292HCID 10109292, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 5-(2-methanesulfonyloxy-ethyl)-2-methyl-1H-indole-3-carboxylic acid benzyl ester (100 mg, 0.26 mmol) in dioxane (5 mL) was added pyrrolidine (0.2 mL, 2.6 mmol). The mixture was stirred at 70° C. for 1 hour and then was concentrated in vacuo to give a residue, which was purified by chromatography (5%-15% methanol in methylene chloride) to give 85 mg (91%) of the desired product as a thick oil: MS(APCI+): m/z 363.2 (MH+).

Workup

  1. concentrationwas concentrated in vacuo
  2. customto give a residue, which
  3. customwas purified by chromatography (5%-15% methanol in methylene chloride)

Sources & evidence

ORD record
ord-5630be18750045ff90928b132fe7c316
Source dataset
uspto-grants-2005_10
Patent number
US06951848B2

Reaction notes

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