Water → methyl 2,3-dihydro-1H-indole-5-carboxylate

HRID 403319Notes

Reaction equation

HRID 403319 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.C([BH3-])#N.[Na+].O.[OH-].[Na+]>C(O)(=O)C>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]([O:12][CH3:13])=[O:11])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 2737635methyl 1H-indole-5-carboxylateHCID 5003444Sodium cyanoborohydride

Product 1

HCID 21782110methyl 2,3-dihydro-1H-indole-5-carboxylateYield 88.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of methyl 1H-indole-5-carboxylate 19a (2 g, 11.4 mmol) in glacial acetic acid (15 mL) at 0° C. was slowly added sodium cyanoborohydride (1.08 g, 17.2 mmol). The mixture was allowed to warm up and stirred at room temperature for 2 h. Water was added to the resulting mixture at 0° C., and the solution was adjusted to pH˜12 with 1N aqueous NaOH. The mixture was extracted with CH2Cl2 and the organic layer was washed with brine and dried over Na2SO4. The solution was concentrated and purified by flash column chromatography (silica gel, 15% EtOAc/heptane) to give compound 24a (1.79 g). MS m/z (M+H+) 178.1.

Workup

  1. customat 0° C.
  2. temperatureto warm up
  3. extractionThe mixture was extracted with CH2Cl2
  4. washthe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationThe solution was concentrated
  7. custompurified by flash column chromatography (silica gel, 15% EtOAc/heptane)

Sources & evidence

ORD record
ord-b4ffcc44fdd9485b9c586bd70a22c751
Source dataset
uspto-grants-2014_06
Patent number
US08748417B2

Reaction notes

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