Triethylamine → 3-(3-Indolyl)-1-propyl methanesulfonate

HRID 1293105Notes

Reaction equation

HRID 1293105 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][CH2:12][OH:13])=[CH:2]1.C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C1COCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][CH2:11][CH2:12][O:13][S:22]([CH3:21])(=[O:24])=[O:23])=[CH:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 77115Indole-3-propanol

Product 1

HCID 115216763-(3-Indolyl)-1-propyl methanesulfonate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

Compound 29 (1.8 g, 5.44 mmol) was transferred to a flame-dried flask filled with argon and dissolved in anhydrous THF then cooled to −40° C. Triethylamine (0.72 g, 7.07 mmol) was added by syringe followed by MeSO2Cl (0.75 g, 6.53 mmol). The temperature of the reaction mixture was allowed to rise to room temperature (10–15 minutes) before it was quickly filtrated and concentrated. The crude oil was dissolved in CH2Cl2 and washed with H2O. The organic phase was dried with MgSO4, filtrated and concentrated in vacuo to a dark, brown oil. The crude product was used immediately in the next step.

Workup

  1. additionfilled with argon
  2. customto rise to room temperature
  3. custom(10–15 minutes)
  4. filtrationwas quickly filtrated
  5. concentrationconcentrated
  6. dissolutionThe crude oil was dissolved in CH2Cl2
  7. washwashed with H2O
  8. dry with materialThe organic phase was dried with MgSO4
  9. filtrationfiltrated
  10. concentrationconcentrated in vacuo to a dark, brown oil

Sources & evidence

ORD record
ord-79128099405f41fbbf262a81997cdf5b
Source dataset
uspto-grants-2007_07
Patent number
US07238713B2

Reaction notes

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