Water → Ethyl 1,3,4,5,6,7-hexahydro-5-methyl-2H-pyrrolo[3,4-c]pyridine-2-carboxylate

HRID 1491656Notes

Reaction equation

HRID 1491656 reaction equation
[I-].[CH2:2]([O:4][C:5]([NH+:7]1[CH2:15][C:14]2[CH:13]=[CH:12][N:11]([CH3:16])[CH2:10][C:9]=2[CH2:8]1)=[O:6])[CH3:3].[BH4-].[Na+].O.C([O-])([O-])=O.[K+].[K+]>CO>[CH3:16][N:11]1[CH2:12][CH2:13][C:14]2[CH2:15][N:7]([C:5]([O:4][CH2:2][CH3:3])=[O:6])[CH2:8][C:9]=2[CH2:10]1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 4311764Sodium borohydrideHCID 678240962-ethoxycarbonyl-5-methyl-2,3-dihydro-1H-pyrrolo[3,4-c]pyridinium iodide

Product 1

HCID 18953646Ethyl 1,3,4,5,6,7-hexahydro-5-methyl-2H-pyrrolo[3,4-c]pyridine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

15.3 g (45.8 mmol) of 2-ethoxycarbonyl-5-methyl-2,3-dihydro-1H-pyrrolo[3,4-c]pyridinium iodide are dissolved in 100 ml of absolute methanol, the solution is cooled to 0° C., and 7 g (0.1 mol) of sodium borohydride are added in 0.5 g portions. The mixture is subsequently stirred for 2 hours at room temperature, 100 ml of water are added, and the mixture is treated with K2CO3 and extracted with CHCl3. The organic solutions are dried over K2CO3 and concentrated, and the residue is distilled.

Workup

  1. extractionextracted with CHCl3
  2. dry with materialThe organic solutions are dried over K2CO3
  3. concentrationconcentrated
  4. distillationthe residue is distilled

Sources & evidence

ORD record
ord-fb1255a00ad847f4ba0f8de58beba895
Source dataset
uspto-grants-1994_12
Patent number
US05371090

Reaction notes

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