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

HRID 450651ノート

反応式

HRID 450651 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-c3a97af5fdf049a49b6795821ec40530
出典データセット
uspto-grants-2013_07
特許番号
US08486979B2

反応ノート

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