Sodium borohydride → 1-(3-(3-(Pyridin-3-yl)-1,2,4-oxadiazol-5-yl)phenyl)ethanol

HRID 450651Notes

Reaction equation

HRID 450651 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:11]=[C:10]([C:12]3[CH:13]=[C:14]([C:18](=[O:20])[CH3:19])[CH:15]=[CH:16][CH:17]=3)[O:9][N:8]=2)[CH:2]=1.[BH4-].[Na+]>C(O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:11]=[C:10]([C:12]3[CH:13]=[C:14]([CH:18]([OH:20])[CH3:19])[CH:15]=[CH:16][CH:17]=3)[O:9][N:8]=2)[CH:2]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 597587481-(3-(3-(Pyridin-3-yl)-1,2,4-oxadiazol-5-yl)phenyl)ethanone

Product 1

HCID 670261921-(3-(3-(Pyridin-3-yl)-1,2,4-oxadiazol-5-yl)phenyl)ethanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the product of Example 68 (265 mg, 1.0 mmol) in ethanol (5 mL) was stirred with sodium borohydride (Aldrich, 83 mg, 2.2 mmol) at room temperature for 16 hours. The inorganic solid was filtered off with a syringe filter and the liquid mixture was purified by preparative HPLC (Gilson, column, Xbridge® 5 μm, 30×100 mm. eluting solvent, acetonitrile/water (pH=10, NH4HCO3—NH3.H2O buffer), v. 5/95 to 95/5 over 35 minutes, flow rate, 40 mL/minute, uv, 234 nm). Fractions of the desired product were collected and concentrated to give the desired product. 1H NMR (300 MHz, CD3OD) δ 1.51 (d, J=6.7 Hz, 3 H), 4.97 (q, J=6.6 Hz, 1 H), 7.57-7.73 (m, 3 H), 8.13 (dt, J=7.6, 1.5 Hz, 1 H), 8.28 (t, J=1.8 Hz, 1 H), 8.57 (dt, J=7.9, 1.8 Hz, 1 H), 8.74 (dd, J=5.0, 1.8 Hz, 1 H), 9.30 (dd, J=2.2, 1.0 Hz, 1 H) ppm; MS (DCI/NH3) m/z 268 (M+H)+.

Workup

  1. filtrationThe inorganic solid was filtered off with a syringe
  2. filtrationfilter
  3. customthe liquid mixture was purified by preparative HPLC (Gilson, column, Xbridge® 5 μm, 30×100 mm. eluting solvent, acetonitrile/water (pH=10, NH4HCO3—NH3.H2O buffer), v. 5/95 to 95/5 over 35 minutes, flow rate, 40 mL/minute, uv, 234 nm)
  4. customFractions of the desired product were collected
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c3a97af5fdf049a49b6795821ec40530
Source dataset
uspto-grants-2013_07
Patent number
US08486979B2

Reaction notes

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