Sodium Bicarbonate → HCID 18355287, compound

HRID 429659Notes

Reaction equation

HRID 429659 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1[NH:11][C:12]2[CH:13]=[CH:14][CH:15]=[C:16]([C:19]([O:21][CH3:22])=[O:20])[C:17]=2[CH:18]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([BH3-])#N.[Na+].C(=O)(O)[O-].[Na+]>CO.Cl.O>[CH2:1]([O:8][CH2:9][CH:10]1[CH2:18][C:17]2[C:16]([C:19]([O:21][CH3:22])=[O:20])=[CH:15][CH:14]=[CH:13][C:12]=2[NH:11]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 18354834HCID 18354834, compound

Product 1

HCID 18355287HCID 18355287, compoundYield 84%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of methyl 2-benzyloxymethylindole-4-carboxylate (650 mg) in methanol (27 ml) and concentrated hydrochloric acid (3.0 ml) was added sodium cyanoborohydride (968 mg) with ice-bath stirring and the mixture was stirred at ambient temperature for 2.5 hours. The resulting mixture was diluted with water (30 ml) and basified with saturated sodium bicarbonate aqueous solution. The mixture was extracted with ethyl acetate (40 ml) and the organic layer was washed successively with water and brine, dried over magnesium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=6:1) to give methyl 2-benzyloxymethylindoline-4-carboxylate (550 mg).

Workup

  1. stirringthe mixture was stirred at ambient temperature for 2.5 hours
  2. extractionThe mixture was extracted with ethyl acetate (40 ml)
  3. washthe organic layer was washed successively with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=6:1)

Sources & evidence

ORD record
ord-3cc94930b54048c9998cb57ca799347e
Source dataset
uspto-grants-2001_11
Patent number
US06316482B1

Reaction notes

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