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

HRID 578142Notes

Reaction equation

HRID 578142 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, 3H), 4.97 (q, J=6.6 Hz, 1H), 7.57-7.73 (m, 3H), 8.13 (dt, J=7.6, 1.5 Hz, 1H), 8.28 (t, J=1.8 Hz, 1H), 8.57 (dt, J=7.9, 1.8 Hz, 1H), 8.74 (dd, J=5.0, 1.8 Hz, 1H), 9.30 (dd, J=2.2, 1.0 Hz, 1H) 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-c8d575aa63334ba094d0f5d459c4c7ae
Source dataset
uspto-grants-2015_05
Patent number
US09040568B2

Reaction notes

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