Sodium borohydride → HCID 67275569, compound

HRID 1698519Notes

Reaction equation

HRID 1698519 reaction equation
[CH:1]1([CH2:4][C:5]([C:7]2[N:11]([CH3:12])[C:10]([S:13][CH2:14][CH:15]3[CH2:17][CH2:16]3)=[N:9][N:8]=2)=[O:6])[CH2:3][CH2:2]1.[BH4-].[Na+]>CO>[CH:1]1([CH2:4][CH:5]([C:7]2[N:11]([CH3:12])[C:10]([S:13][CH2:14][CH:15]3[CH2:17][CH2:16]3)=[N:9][N:8]=2)[OH:6])[CH2:2][CH2:3]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57959870HCID 57959870, compound

Product 1

HCID 67275569HCID 67275569, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
4 °C

Procedure

The crude 2-cyclopropyl-1-{5-[(cyclopropylmethyl)thio]-4-methyl-4H-1,2,4-triazol-3-yl}ethanone (817 mg, 3.25 mmol) was dissolved in methanol (20 mL) and the mixture cooled in an ice bath (4° C.). Sodium borohydride (285 mg, 7.5 mmol) was added portionwise and the reaction mixture stirred at 4° C. for 30 min and then at room temperature for 2 h. Solvent was removed in vacuo and the residue purified by chromatography on silica eluting with ethyl acetate to give the title compound (578 mg, 24% yield over 2 steps). 1H NMR (500 MHz, CDCl3) δ (ppm) 4.91 (1H, s), 3.75 (1H, s), 3.65 (3H, s), 3.11 (2H, d, J=7.3 Hz), 1.98-1.90 (1H, m), 1.84-1.78 (1H, m), 1.20-1.12 (1H, m), 0.88-0.80 (1H, m), 0.62-0.58 (2H, m), 0.53-0.43 (2H, m), 0.29-0.26 (2H, m), 0.18-0.12 (1H, m), 0.08-0.04 (1H, m).

Workup

  1. waitat room temperature for 2 h
  2. customSolvent was removed in vacuo
  3. customthe residue purified by chromatography on silica eluting with ethyl acetate

Sources & evidence

ORD record
ord-b1d1f66025ab48589d0dec13e53c1498
Source dataset
uspto-grants-2012_04
Patent number
US08163956B2

Reaction notes

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