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

HRID 578142노트

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HRID 578142 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-c8d575aa63334ba094d0f5d459c4c7ae
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09040568B2

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