Diisopropylethylamine → HCID 68702130, compound

HRID 2235098Notes

Reaction equation

HRID 2235098 reaction equation
[C:1](=[O:12])([O:7][C:8]([CH3:11])([CH3:10])[CH3:9])OC(C)(C)C.[CH3:13][O:14][C:15]([C:17]1[CH:25]=[C:24]2[C:20]([CH2:21][CH2:22][NH:23]2)=[C:19]([O:26][CH3:27])[CH:18]=1)=[O:16].C(N(C(C)C)CC)(C)C>O1CCCC1>[CH3:13][O:14][C:15]([C:17]1[CH:25]=[C:24]2[C:20]([CH2:21][CH2:22][N:23]2[C:1]([O:7][C:8]([CH3:9])([CH3:10])[CH3:11])=[O:12])=[C:19]([O:26][CH3:27])[CH:18]=1)=[O:16]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) esterHCID 68701783HCID 68701783, compound

Product 1

HCID 68702130HCID 68702130, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Di-tert-butyl carbonate (2.9 g, 13.5 mmol, 1 equiv.) was added to a stirred mixture of 4-methoxy-2,3-dihydro-1H-indole-6-carboxylic acid methyl ester (2.8 g 13.5 mmol, 1 equiv.) and diisopropyl ethyl amine (4.7 mL, 27 mmol, 2 equiv.) in tetrahydrofuran (30 mL) and the mixture was heated at reflux for 16 hours. The solvent was evaporated under vacuum and the residue purified by column chromatography (SiO2, 1:8 EtOAc:heptane). The fractions were combined to afford 4-methoxy-2,3-dihydro-indole-1,6-dicarboxylic acid 1-tert-butyl ester 6-methyl ester, 1.96 g (47% yield). δH (250 MHz; d6-DMSO) 7.80 (1H, s), 7.10 (1H, s), 3.96 (2H, t), 3.78 (6H, s), 3.03 (2H, t), 1.45 (9H, m).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 16 hours
  3. customThe solvent was evaporated under vacuum
  4. customthe residue purified by column chromatography (SiO2, 1:8 EtOAc:heptane)

Sources & evidence

ORD record
ord-58dd4cabee234523b5340ca667a13010
Source dataset
uspto-grants-2010_05
Patent number
US07713996B2

Reaction notes

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