Sodium cyanoborohydride → Methyl 1-butylindoline-6-carboxylate

HRID 14159

Reaction equation

HRID 14159 reaction equation
[CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[CH:12]=2)[CH:7]=[CH:6]1)[CH2:2][CH2:3][CH3:4].C([BH3-])#N.[Na+]>C(O)(=O)C>[CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:14]([O:16][CH3:17])=[O:15])[CH:12]=2)[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 21086134methyl 1-butyl-1H-indole-6-carboxylate

Product 1

HCID 21086137Methyl 1-butylindoline-6-carboxylateYield 77.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture of methyl 1-butyl-1H-indole-6-carboxylate, (2.1 g) in glacial acetic acid (25 mL) was added sodium cyanoborohydride (2.28 g). The mixture was heated at 40° C. for 3 h then cooled to room temperature, partitioned between water and ethyl acetate and the layers were separated. The organic layer was washed three times with brine, dried over anhydrous sodium sulfate and concentrated to give 1.64 g of the title compound: 1H NMR (CDCl3) δ 0.969, 1.43, 1.59, 2.99, 3.1, 3.4, 3.88, 7.07, 7.34.

Workup

  1. temperaturethen cooled to room temperature
  2. custompartitioned between water and ethyl acetate
  3. customthe layers were separated
  4. washThe organic layer was washed three times with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ec36e4517aeb4f9583456d798cf68415
Source dataset
uspto-grants-2010_06
Patent number
US07727997B2

Linked notes

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