Ammonium Chloride → 2,3-dihydro-2-(hydroxymethyl)-1H-pyrrolo[1,2-a]indole

HRID 863683Notes

Reaction equation

HRID 863683 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]1[C:11]2=[CH:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][C:18]=3[N:10]2[CH2:9][CH:8]1[C:19](OCC)=[O:20].[Cl-].[NH4+]>O1CCCC1>[OH:20][CH2:19][CH:8]1[CH2:9][N:10]2[C:18]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH:12]=[C:11]2[CH2:7]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 19696125HCID 19696125, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 196963632,3-dihydro-2-(hydroxymethyl)-1H-pyrrolo[1,2-a]indoleYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4 ml of a 1M solution of lithium aluminum hydride in tetrahydrofuran were added to a solution of 750 mg of ethyl 2,3-dihydro-1H-pyrrolo[1,2-a]indole-2-carboxylate in 30 ml of tetrahydrofuran. After 1 hour, 30 ml of saturated ammonium chloride solution were added and the mixture was evaporated. The residue was extracted with dichloromethane and the organic extract was dried and evaporated. Crystallization of the residue from diethyl ether/petroleum ether gave 355 mg of 2,3-dihydro-2-(hydroxymethyl)-1H-pyrrolo[1,2-a]indole of melting point 76°-78° C.

Workup

  1. customthe mixture was evaporated
  2. extractionThe residue was extracted with dichloromethane
  3. extractionthe organic extract
  4. customwas dried
  5. customevaporated
  6. customCrystallization of the residue from diethyl ether/petroleum ether

Sources & evidence

ORD record
ord-1b4a2dc1665745f19420c6cad0c925f0
Source dataset
uspto-grants-1998_02
Patent number
US05721245

Reaction notes

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