Sodium borohydride → (5-Bromo-2-(2-methylpiperidin-1-YL)phenyl)methanol

HRID 1630968

반응식

HRID 1630968 반응식
[BH4-].[Na+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]2[CH3:18])=[C:8]([CH:11]=1)[CH:9]=[O:10]>CO.[NH4+].[Cl-]>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([N:12]2[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]2[CH3:18])=[C:8]([CH2:9][OH:10])[CH:11]=1

참가 물질

5

반응물 2

HCID 4311764Sodium borohydrideHCID 230911015-Bromo-2-(2-methylpiperidin-1-YL)benzaldehyde

생성물 1

HCID 58554197(5-Bromo-2-(2-methylpiperidin-1-YL)phenyl)methanol수율 97%

시약·촉매·용매 2

HCID 887Methanol용매HCID 25517Ammonium Chloride용매

반응 조건

온도
5 °C

실험 절차

Sodium borohydride (2.2 g, 57.8 mmol) was added portion-wise into a solution of 5-bromo-2-(2-methylpiperidin-1-yl)benzaldehyde (16.3 g, 57.8 mmol) in MeOH (300 mL) cooled at 5° C. After 30 min, the reaction mixture was diluted with a saturated aqueous solution of NH4Cl (300 mL) and extracted with EtOAc (600 mL+300 mL). The organic layers were washed with a saturated aqueous solution of NH4Cl (150 mL) and brine (300 mL). The organic layers were combined, dried (MgSO4) and the solvents were removed under reduced pressure to give the title compound as a yellow oil (15.9 g, 97%) used without further purification in the next step. HPLC (Method A), Rt 2.1 min (Purity: 94.9%). UPLC/MS, M+(ESI): 284.1, 286.0. 1H NMR (CDCl3, 300 MHz) δ 7.38 (dd, J=8.5, 2.4 Hz, 1H), 7.26 (d, J=2.4 Hz, 1H), 7.13 (d, J=8.5 Hz, 1H), 6.40 (brs, 1H), 4.86 (d, J=13.9 Hz, 1H), 4.67 (d, J=13.9 Hz, 1H), 3.06-2.88 (m, 2H), 2.61 (td, J=11.4, 3.2 Hz, 1H), 1.88-1.58 (m, 4H), 1.53-1.32 (m, 2H), 0.90 (d, J=6.2 Hz, 3H).

후처리

  1. extractionextracted with EtOAc (600 mL+300 mL)
  2. washThe organic layers were washed with a saturated aqueous solution of NH4Cl (150 mL) and brine (300 mL)
  3. dry with materialdried (MgSO4)
  4. customthe solvents were removed under reduced pressure

출처 및 근거

ORD 기록
ord-b559cc17ebc64fb9ae8e7d22fbd0cf52
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08791142B2

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