Triethylamine → HCID 86590909, compound

HRID 985641Notes

Reaction equation

HRID 985641 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][OH:18])=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[CH3:26][S:27](Cl)(=[O:29])=[O:28]>ClCCl>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH2:17][O:18][S:27]([CH3:26])(=[O:29])=[O:28])=[CH:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11075767tert-Butyl 3-(hydroxymethyl)-1H-indole-1-carboxylate

Product 1

HCID 86590909HCID 86590909, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A well-stirred solution of 3-hydroxymethyl-indole-1-carboxylic acid tert-butyl ester (10, 450 mg, 1.82 mmol) [as prepared following the procedure of D. J. Oliveira and F. Coelho, Synth. Commun. 30 (12) pg. 2143 (2000)] in 10 mL of dichloromethane was cooled in an ice-bath, then treated successively with triethylamine (TEA) (283 mg, 2.18 mmole) and methanesulfonyl chloride (229 mg, 2.0 mmol). This was allowed to stir under nitrogen for 15 min. diluted with dichloromethane, then washed with saturated NaHCO3, dried (Na2SO4) and evaporated. This residue was purified by chromatography to give 0.43 g (73% yield) of the desired compound as an unstable brown solid. 1H NMR (CDCl3) δ 1.67 (s, 12H), 4.79 (s, 2H), 7.28 (t, 1H), 7.36 (t, 1H), 7.67 (m, 2H), 7.51 (bd, 1H).

Workup

  1. washwashed with saturated NaHCO3
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customThis residue was purified by chromatography

Sources & evidence

ORD record
ord-aa65ff55f2154e9da761266426ee4c9c
Source dataset
uspto-grants-2005_03
Patent number
US06872827B2

Reaction notes

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