Sodium borohydride → HCID 59526202, compound

HRID 386078Notes

Reaction equation

HRID 386078 reaction equation
[BH4-].[Na+].C[O:4][C:5](=O)[CH2:6][N:7]1[N:11]=[N:10][C:9]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[N:14]=2)=[N:8]1>CO.O>[Br:19][C:15]1[N:14]=[C:13]([CH2:12][C:9]2[N:10]=[N:11][N:7]([CH2:6][CH2:5][OH:4])[N:8]=2)[CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 59525562HCID 59525562, compound

Product 1

HCID 59526202HCID 59526202, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of NaBH4 (92 mg, 2.44 mmol) in MeOH (4.0 mL) at room temperature was added methyl{5-[(6-bromopyridin-2-yl)methyl]-2H-tetrazol-2-yl}acetate (380 mg, 1.22 mmol) in MeOH (6.0 mL). The reaction was stirred at room temperature for 2 h. It was then diluted with water and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried (MgSO4), filtered, and evaporated. Flash chromatography (40-100% EtOAc/hexanes) afforded the title compound as a colorless gum.

Workup

  1. extractionextracted with EtOAc (3×)
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-929b2e7a8bbb490492eca61a3fe11cf3
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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