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

HRID 1168849Notes

Reaction equation

HRID 1168849 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-2117d8cd2a5042c6a2fdfb55cf2d79cb
Source dataset
uspto-grants-2003_09
Patent number
US06627645B2

Reaction notes

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