Triethylamine → N-(methanesulfonyl)-3-(octahydroindolizin-7-yl)-5-amino-1H-indole

HRID 363333Notes

Reaction equation

HRID 363333 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]1[CH:14]2[N:9]([CH2:10][CH2:11][CH:12]([C:15]3[C:23]4[C:18](=[CH:19][CH:20]=[C:21]([NH2:24])[CH:22]=4)[NH:17][CH:16]=3)[CH2:13]2)[CH2:8][CH2:7]1.C(N(CC)CC)C.[OH-].[NH4+]>CN(C)C=O.CO.C(Cl)Cl.O>[CH3:1][S:2]([N:17]1[C:18]2[C:23](=[CH:22][C:21]([NH2:24])=[CH:20][CH:19]=2)[C:15]([CH:12]2[CH2:13][CH:14]3[N:9]([CH2:8][CH2:7][CH2:6]3)[CH2:10][CH2:11]2)=[CH:16]1)(=[O:4])=[O:3]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 14923Ammonium HydroxideHCID 31297Methanesulfonyl chlorideHCID 153897613-(Octahydroindolizin-7-yl)-5-amino-1H-indole

Product 1

HCID 67570698N-(methanesulfonyl)-3-(octahydroindolizin-7-yl)-5-amino-1H-indoleYield 50.4%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

The methanesulfonyl chloride (215 mg, 1.87 mmol) was added dropwise to a solution of the 3-(octahydroindolizin-7-yl)-5-amino-1H-indole (320 mg, 1.25 mmol) and triethylamine (0.5 ml) in 10 ml of dimethylformamide. The reaction was stirred at room temperature for 2.5 hours. The reaction was diluted with methanol and concentrated to give a dark semi-solid. This material was dissolved in a mixture of methylene chloride and water, made basic with an ammonium hydroxide solution, then extracted with methylene chloride. The extract was dried over sodium sulfate and concentrated to give a reddish brown oil. The material was purified on a flash column using silica gel (20% methanol in methylene chloride (ammonium hydroxide) as eluent) to give 210 mg of product. (49.7%).

Workup

  1. concentrationconcentrated
  2. customto give a dark semi-solid
  3. extractionextracted with methylene chloride
  4. dry with materialThe extract was dried over sodium sulfate
  5. concentrationconcentrated
  6. customto give a reddish brown oil
  7. customThe material was purified on a flash column

Sources & evidence

ORD record
ord-c0fcbeb6fa764235875a3d60b1dc7306
Source dataset
uspto-grants-1999_02
Patent number
US05874427

Reaction notes

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