Sodium Hydroxide → [2-(Methylamino)pyridin-3-yl]methanol

HRID 859240ノート

反応式

HRID 859240 の反応式
[CH3:1][NH:2][C:3]1[N:15]=[CH:14][CH:13]=[CH:12][C:4]=1[C:5](OC(C)(C)C)=[O:6].[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1.O>[OH:6][CH2:5][C:4]1[C:3]([NH:2][CH3:1])=[N:15][CH:14]=[CH:13][CH:12]=1

参加物

7

反応物 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydride2 回HCID 22645509HCID 22645509、化合物

生成物 1

HCID 4738518[2-(Methylamino)pyridin-3-yl]methanol収率 76.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of t-butyl 2-(methylamino)nicotinate (45.0 g, 0.216 mol) in dry THF (500 mL) cooled in an ice-bath was added LiAlH4 (9.84 g, 0.259 mol) portionwise over a period of 30 min. After stiring for 1 h at 0° C., the mixture was warmed to room temperature and stirred for 2 h. After cooling in an ice-bath, the excess LiAlH4 was decomposed completely by the careful addition of H2O (10 mL) and 1N NaOH aqueous solution (10 mL). Na2SO4 (100 g) was added and the mixture was filtered through a pad of celite. The filtrate was evaporated under reduced pressure and the resulting residue was purified by column chromatography (400 g of silica gel, eluent: DCM/MeOH=20/1−10/1) to give the desire product which was further purified by recrystallization from DCM-hexane to give 3-hydroxymethyl-2-(N-methylamino)pyridine (m) (22.7 g, 76%); 1H NMR (CDCl3): δ 2.30 (brs, 1H), 3.01 (d, J=4.6 Hz, 3H), 4.58 (s, 2H), 5.40 (brs, 1H), 6.50 (dd, J=5.1 and 7.3 Hz, 1H), 7.21 (dd, J=1.7 and 7.3 Hz, 1H), 8.08 (dd, J=1.7 and 5.1 Hz, 1H).

後処理

  1. temperatureAfter cooling in an ice-bath
  2. filtrationthe mixture was filtered through a pad of celite
  3. customThe filtrate was evaporated under reduced pressure
  4. customthe resulting residue was purified by column chromatography (400 g of silica gel, eluent: DCM/MeOH=20/1−10/1)
  5. customto give the desire product which
  6. customwas further purified by recrystallization from DCM-hexane

出典と根拠

ORDレコード
ord-808b7577b0d94b38a0308b7113b87761
出典データセット
uspto-grants-2006_12
特許番号
US07151182B2

反応ノート

読み込み中…