Acetic Acid → 1-Tert-butyl 2-ethyl 7-(cyclopropylamino)-5-(2-methoxyethoxy)indoline-1,2-dicarboxylate

HRID 1960443Notes

Reaction equation

HRID 1960443 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([O:23][CH2:24][CH2:25][O:26][CH3:27])[CH:5]=[C:6]2[C:10]=1[N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH:8]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:7]2.C(O[C:31]1(O[Si](C)(C)C)[CH2:33][CH2:32]1)C.C(O)(=O)C.C([BH3-])#N.[Na+]>C(O)C>[CH:31]1([NH:1][C:2]2[CH:3]=[C:4]([O:23][CH2:24][CH2:25][O:26][CH3:27])[CH:5]=[C:6]3[C:10]=2[N:9]([C:11]([O:13][C:14]([CH3:16])([CH3:15])[CH3:17])=[O:12])[CH:8]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH2:7]3)[CH2:33][CH2:32]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 5003444Sodium cyanoborohydrideHCID 59303538HCID 59303538, compound

Product 1

HCID 593035091-Tert-butyl 2-ethyl 7-(cyclopropylamino)-5-(2-methoxyethoxy)indoline-1,2-dicarboxylateYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 1-tert-butyl 2-ethyl 7-amino-5-(2-methoxyethoxy)indoline-1,2-dicarboxylate (2.76 g), [(1-ethoxycyclopropyl)oxy](trimethyl)silane (7.29 mL), acetic acid (4.19 mL) and ethanol (70 mL) was added sodium cyanoborohydride (122 mg), and the mixture was refluxed for 3 hr. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate and water. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and filtered, and the filtrate was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give the title compound (2.30 g, yield 75%) as a pale-yellow oil from a fraction eluted with ethyl acetate-hexane (4:1, volume ratio).

Workup

  1. temperaturethe mixture was refluxed for 3 hr
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionthe residue was diluted with ethyl acetate and water
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-eecec331023e42bbbb322c1c5c01701a
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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