Hydrochloric Acid → HCID 54381464, compound

HRID 429649Notes

Reaction equation

HRID 429649 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])[C:11]=2[C:10]([CH:27]=[O:28])=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+].Cl>CO.O>[C:1]([O:5][C:6]([N:8]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([C:17]([O:19][CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:18])[C:11]=2[C:10]([CH2:27][OH:28])=[CH:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 86756565HCID 86756565, compound

Product 1

HCID 54381464HCID 54381464, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of benzyl 1-tert-butoxycarbonyl-3-formylindole-4-carboxylate (363 mg) in methanol (15 ml) was added sodium borohydride (109 mg) at 0° C. and the mixture was stirred for 5 minutes. The resulting mixture was diluted with water and the solution was neutralized with 1N hydrochloric acid. The solution was extracted with ethyl acetate, and then the organic solution was washed successively with saturated sodium bicarbonate aqueous solution and brine, dried over magnesium sulfate and concentrated in vacuo to afford benzyl 1-tert-butoxycarbonyl-3-hydroxymethylindole-4-carboxylate (365 mg).

Workup

  1. extractionThe solution was extracted with ethyl acetate
  2. washthe organic solution was washed successively with saturated sodium bicarbonate aqueous solution and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7eb734491451465daf8e4d5599540f56
Source dataset
uspto-grants-2001_11
Patent number
US06316482B1

Reaction notes

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