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

HRID 401694Notes

Reaction equation

HRID 401694 reaction equation
C1(C2[CH:12]=[CH:11][C:10]([C:13]([N:15]3[CH2:18][CH:17](N4CCNCC4)[CH2:16]3)=O)=CC=2)CCCCC1.[C:25]([BH3-])#N.[Na+].O.[OH-].[Na+].[C:32]([OH:35])(=[O:34])[CH3:33]>>[NH:15]1[C:18]2[C:11](=[CH:12][C:33]([C:32]([O:35][CH3:25])=[O:34])=[CH:16][CH:17]=2)[CH2:10][CH2:13]1

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 59626057(4-Cyclohexyl-phenyl)-(3-piperazin-1-yl-azetidin-1-yl)-methanone

Product 1

HCID 21782110methyl 2,3-dihydro-1H-indole-5-carboxylate

Procedure

To a solution of methyl 1H-indole-5-carboxylate 1j (2 g, 11.4 mmol) in glacial acetic acid (15 mL) at 0° C. was added sodium cyanoborohydride (1.08 g, 17.2 mmol) slowly. 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 pH of the solution was adjusted to ˜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 55a (1.79 g). MS m/z (M+H+) 178.1.

Workup

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

Sources & evidence

ORD record
ord-bd467c153d4b41d8a47d75301e15687c
Source dataset
uspto-grants-2014_06
Patent number
US08741887B2

Reaction notes

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