Sodium Bicarbonate → HCID 86701158, compound

HRID 1396669Notes

Reaction equation

HRID 1396669 reaction equation
[CH:1]([C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][N:6]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]2)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[CH3:33][NH:34][CH3:35].O1CCCC1.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.ClCCCl.C(O)(=O)C>[CH3:33][N:34]([CH2:1][C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[CH2:5][N:6]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]2)[CH3:35]

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 22320367Dimethylamine tetrahydrofuranHCID 509991201,1-Dimethylethyl 4-formyl-1,3-dihydro-2H-isoindole-2-carboxylate

Product 1

HCID 86701158HCID 86701158, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 238 mg of tert-butyl 4-formyl-1,3-dihydro-2H-isoindole-2-carboxylate, 612 mg of sodium triacetoxyborohydride, 963 μL of a 2 M dimethylamine-tetrahydrofuran solution, 12 μL of acetic acid, and 14 mL of 1,2-dichloroethane was stirred at 60° C. overnight. After cooling to room temperature, to the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution, and chloroform was added and the aqueous layer was separated. The obtained organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to obtain 123 mg of tert-butyl 4-[(dimethylamino)methyl]-1,3-dihydro-2H-isoindole-2-carboxylate as an orange oil.

Workup

  1. temperatureAfter cooling to room temperature, to the reaction mixture
  2. additionwas added
  3. customthe aqueous layer was separated
  4. washThe obtained organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-61c37b59b1ee44c2953c90ee6aade00d
Source dataset
uspto-grants-2014_12
Patent number
US08901126B2

Reaction notes

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