Triethylamine → 2,3-Dihydro-1H-pyrrolo[1,2-a]indole

HRID 863543Notes

Reaction equation

HRID 863543 reaction equation
Cl.[CH2:2]1[C:6]2=[CH:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[N:5]2[CH2:4][CH2:3]1.C(OC(OC(OC(C)(C)C)=O)=O)(C)(C)C.C(N(CC)CC)C>ClCCl>[CH2:2]1[C:6]2=[CH:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[N:5]2[CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 90495Di-tert-butyl dicarbonateHCID 1317205392,3-dihydro-1H-pyrrolo[1,2-a]indole hydrochloride

Product 1

HCID 110008472,3-Dihydro-1H-pyrrolo[1,2-a]indole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 100 mg (0.38 mmol) of 2(R or S)-[1(R or S)-amino-2-methylpropyl]-2,3-dihydro-1H-pyrrolo[1,2-a]indole hydrochloride (diastereomer A) in 30 ml of dichloromethane was treated with 110 mg (0.5 mmol) of di-tert.butyldicarbonate and 100 mg (1 mmol) of triethylamine and stirred for 72 hours. The solution was washed in succession with 30 ml of 1M hydrochloric acid and 30 ml of saturated aqueous sodium bicarbonate and then dried over magnesium sulfate. After filtration, concentration of the filtrate under reduced pressure and purification of the residue by flash chromatography using diethyl ether/petroleum ether (b.p. 40°-60° C.) (1:2) for the elution gave 100 mg of tert.butyl [1(R or S)-[2,3-dihydro-1H-pyrrolo[1,2-a]indol-2-(R or S)-yl]-2-methylpropyl]carbamate (diastereomer A) in the form of an oil.

Workup

  1. washThe solution was washed in succession with 30 ml of 1M hydrochloric acid and 30 ml of saturated aqueous sodium bicarbonate
  2. dry with materialdried over magnesium sulfate
  3. filtrationAfter filtration, concentration of the filtrate
  4. customunder reduced pressure and purification of the residue by flash chromatography
  5. washfor the elution

Sources & evidence

ORD record
ord-93b140a91688461ea2c822ecd6fb4eb9
Source dataset
uspto-grants-1998_02
Patent number
US05721230

Reaction notes

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