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

HRID 1630968

反応式

HRID 1630968 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 25517Ammonium Chloride溶媒

反応条件

温度
5 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-b559cc17ebc64fb9ae8e7d22fbd0cf52
出典データセット
uspto-grants-2014_07
特許番号
US08791142B2

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