Ethanethiol → 1H-Indole, 5-bromo-3-(2-pyrrolidinylmethyl)-, (R)-

HRID 1441078Notes

Reaction equation

HRID 1441078 reaction equation
C(OC([N:11]1[CH2:15][CH2:14][CH2:13][C@@H:12]1[CH2:16][C:17]1[C:25]2[C:20](=[CH:21][CH:22]=[C:23]([Br:26])[CH:24]=2)[NH:19][CH:18]=1)=O)C1C=CC=CC=1.B(F)(F)F.C(S)C.C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[NH3:11].[Br:26][C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][CH:22]=1)[NH:19][CH:18]=[C:17]2[CH2:16][C@H:12]1[CH2:13][CH2:14][CH2:15][NH:11]1

Participants

7

Reactant 4

HCID 6343EthanethiolHCID 6356Boron trifluorideHCID 10340Sodium CarbonateHCID 22859561(R)-Benzyl 2-((5-bromo-1H-indol-3-yl)methyl)pyrrolidine-1-carboxylate

Product 2

HCID 222AmmoniaHCID 228595901H-Indole, 5-bromo-3-(2-pyrrolidinylmethyl)-, (R)-Yield 124.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(1-Benzyloxycarbonylpyrrolidin-2(R)-ylmethyl)-5-bromo-1H-indole (see Preparation 35B) (5.00 g, 12.10 mmol) was dissolved in dichioromethane and the resulting solution was added dropwise to a stirred mixture of boron-trifluoride.etherate (17.15 g, 14.9 ml, 12.1 mmol) and ethane thiol (21.4 g, 25.5 ml, 344 mmol) at room temperature under nitrogen. After 68 hours the reaction mixture was added by pipette to a 10% aqueous sodium carbonate solution (500 ml) and extracted with ethyl acetate (3×400 ml). The combined organic extract was dried (Na2SO4) and the solvent evaporated under reduced pressure. Purification by column chromatography on silica gel, eluting with dichioromethane: methanol:0.880 aqueous ammonia (90:10:1), yielded the title compound as a foam (2.1 g). Found: C,55.04; H,5.29; N,9.83. C13H15BrN2.3/50CH2Cl2 requires: C,55.10; H,5.35; N,9.83%.

Workup

  1. customat room temperature
  2. extractionextracted with ethyl acetate (3×400 ml)
  3. extractionThe combined organic extract
  4. dry with materialwas dried (Na2SO4)
  5. customthe solvent evaporated under reduced pressure
  6. customPurification by column chromatography on silica gel
  7. washeluting with dichioromethane

Sources & evidence

ORD record
ord-79f8f4b5b332432cb5f974d231b12aed
Source dataset
uspto-grants-1996_03
Patent number
US05502065

Reaction notes

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