Sodium Bicarbonate → METHYL 1-(3-methoxypropyl)indoline-6-carboxylate

HRID 922442Notes

Reaction equation

HRID 922442 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([O:17][CH3:18])=[O:16])[CH:13]=2)[CH:8]=[CH:7]1.[Na].C(=O)([O-])O.[Na+]>C(O)(=O)C>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15]([O:17][CH3:18])=[O:16])[CH:13]=2)[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 516892Sodium Bicarbonate2×HCID 5360545SodiumHCID 67542758methyl 1-(3-methoxypropyl)-1H-indole-6-carboxylate

Product 1

HCID 86707862METHYL 1-(3-methoxypropyl)indoline-6-carboxylate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of methyl 1-(3-methoxypropyl)-1H-indole-6-carboxylate (1.5 g) and sodium cyanohydroborate (1.61 g) was added acetic acid (15 mL) under ice-cooling, and the mixture was stirred at room temperature for 3 hours. To the reaction solution was added aqueous saturated sodium hydrogen carbonate solution under ice-cooling, and the mixture was neutralized by adding sodium hydrogen carbonate, and then extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over sodium sulfate, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane→n-hexane/ethyl acetate=2/1) to give methyl 1-(3-methoxypropyl)indoline-6-carboxylate [REx(10-1)] (1.20) as a pale yellow oil.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated saline
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane→n-hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-ca05ce8e204c426393431c2055c8f0a7
Source dataset
uspto-grants-2016_03
Patent number
US09278944B2

Reaction notes

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