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

HRID 1852648Notes

Reaction equation

HRID 1852648 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-bcb1e1d8f90a4c388ac9435c7fd5ac94
Source dataset
uspto-grants-2015_02
Patent number
US08962607B2

Reaction notes

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