Methanol → HCID 68698202, compound

HRID 2235099Notes

Reaction equation

HRID 2235099 reaction equation
[OH-].[K+].C[O:4][C:5]([C:7]1[CH:15]=[C:14]2[C:10]([CH2:11][CH2:12][N:13]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[C:9]([O:23][CH3:24])[CH:8]=1)=[O:6].CO>O1CCCC1>[C:19]([O:18][C:16]([N:13]1[C:14]2[C:10](=[C:9]([O:23][CH3:24])[CH:8]=[C:7]([C:5]([OH:6])=[O:4])[CH:15]=2)[CH2:11][CH2:12]1)=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 68702130HCID 68702130, compound

Product 1

HCID 68698202HCID 68698202, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 3 N aqueous KOH solution (6.5 mL, 19.5 mmol, 3 equiv.) was added to a solution of 4-methoxy-2,3-dihydro-indole-1,6-dicarboxylic acid 1-tert-butyl ester 6-methyl ester (2 g, 6.5 mmol, 1 equiv.) in a 1:4 MeOH:tetrahydrofuran solution (20 mL) and the mixture was shaken for 16 hours. The methanol was removed under vacuum and the pH was adjusted to 3 with 3 N aqueous HCl solution. The resulting slurry was diluted with ethyl acetate (20 mL), the organic layer was separated and the aqueous phase was extracted with EtOAc (2×20 mL). The organic layers were combined, dried over Na2SO4 and the solvent was removed under vacuum to afford 4-methoxy-2,3-dihydro-indole-1,6-dicarboxylic acid 1-tert-butyl ester, 1.68 g (88% yield). LC @215 nm; Rt 1.44: 83%, m/z (ES+): 238 (M-Boc+MeCN+H+.); δH (400 MHz; d6-DMSO) 12.58 (1H, br.s) 7.97 (1H, br.s), 6.94 (1H, d), 3.70 (2H, t), 3.61 (3H, s), 2.75 (2H, t), 1.28 (9H, s).

Workup

  1. customThe methanol was removed under vacuum
  2. additionThe resulting slurry was diluted with ethyl acetate (20 mL)
  3. customthe organic layer was separated
  4. extractionthe aqueous phase was extracted with EtOAc (2×20 mL)
  5. dry with materialdried over Na2SO4
  6. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-e0988801369f4744999a85b8d873916e
Source dataset
uspto-grants-2010_05
Patent number
US07713996B2

Reaction notes

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