Potassium Hydroxide → 2287238-27-9

HRID 1257627

反応式

HRID 1257627 の反応式
COC(=O)[NH:4][C@H:5]1[C@@H:10]([CH3:11])[CH2:9][CH2:8][N:7]([CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:6]1.[OH-].[K+]>CO.O>[CH2:12]([N:7]1[CH2:8][CH2:9][C@H:10]([CH3:11])[C@H:5]([NH2:4])[CH2:6]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

参加物

5

反応物 2

HCID 14797Potassium HydroxideHCID 56832346Methyl ((3S,4S)-1-benzyl-4-methylpiperidin-3-yl)carbamate

生成物 1

HCID 685920612287238-27-9収率 38%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

A mixture of racemic cis (1-benzyl-4-methyl-piperidin-3-yl)-carbamic acid methyl ester (1.56 g, 5.95 mmol) and potassium hydroxide (9.90 mL, 59.5 mmol, 6M solution) in methanol (50 mL) was heated at reflux for 48 hours. The cooled reaction mixture was diluted with water and extracted with ethyl acetate. The combined organic phases were washed with brine then dried over sodium sulfate and concentrated under vacuum. The resulting residue was purified by column chromatography on silica gel (gradient: 0 to 7% 2M NH3 in methanol solution in DCM) to afford 460 mg (38%) of racemic cis 1-benzyl-4-methyl-piperidin-3-ylamine. LCMS (Method H, ESI): RT=0.35 min, m+H=204.9; 1H NMR (400 MHz, CDCl3) δ: 7.29-7.28 (m, 5H), 3.45 (s, 2H), 2.76-2.72 (m, 3H), 2.20-2.11 (m, 1H), 1.97 (td, 1H), 1.42 (m, 5H), 0.91 (d, 3H).

後処理

  1. temperaturewas heated
  2. temperatureat reflux for 48 hours
  3. customThe cooled reaction mixture
  4. extractionextracted with ethyl acetate
  5. washThe combined organic phases were washed with brine
  6. dry with materialthen dried over sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customThe resulting residue was purified by column chromatography on silica gel (gradient: 0 to 7% 2M NH3 in methanol solution in DCM)

出典と根拠

ORDレコード
ord-5543dab3bf9a45428089b861327a1e1d
出典データセット
uspto-grants-2013_06
特許番号
US08461328B2

関連ノート

読み込み中…