Sodium borohydride → HCID 67265589, compound

HRID 1685745Notes

Reaction equation

HRID 1685745 reaction equation
[CH:1]([C:3]1[S:7][C:6]([C:8]2[N:9]=[N:10][O:11][CH:12]=2)=[CH:5][CH:4]=1)=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[BH3-]C#[N:29].[Na+].[BH4-].[Na+]>CO.O.C(O)=O>[NH2:29][CH2:1][C:3]1[S:7][C:6]([C:8]2[N:9]=[N:10][O:11][CH:12]=2)=[CH:5][CH:4]=1

Participants

8

Reactant 4

HCID 4311764Sodium borohydrideHCID 5003444Sodium cyanoborohydrideHCID 5049666Sodium triacetoxyborohydrideHCID 86646448HCID 86646448, compound

Product 1

HCID 67265589HCID 67265589, compound

Reagents, catalysts & solvents 3

HCID 284Formic AcidSolventHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of the 5-formyl-thiophen-2-yl-oxadiazol derivative (1 eq., usual scale 0.02-0.25 mmol) and the appropriate amine (2-40 eq.) in methanol (24 mL/mmol), sodium triacetoxy borohydride (NaBH(OAc)3) (10 eq.) is added. The mixture is stirred for 2 h before NaBH3CN (10 eq.) is added. Stirring of the suspension is continued for 16 h before NaBH4 (20 eq.) is added and stirring is continued for another 16 h at rt. The reaction mixture is diluted with water (4 mL/mmol) and formic acid (4 mL/mmol) and the resulting solution is separated by prep. HPLC (Waters Symmetry C18 19×50 mm, 5 μm, 10 to 95% acetonitrile in water containing 0.5% HCOOH) to give the desired 5-aminomethyl-thiophen-2-yl-oxadiazol derivative as a colourless to pale yellow resin.

Workup

  1. additionis added
  2. additionis added
  3. stirringstirring
  4. customthe resulting solution is separated by prep

Sources & evidence

ORD record
ord-18d412daa6e84e45a80f580647e11457
Source dataset
uspto-grants-2012_04
Patent number
US08148410B2

Reaction notes

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