Hydrochloric Acid → 3-Amino-3-methylpiperidine-2,6-dione hydrochloride

HRID 651437ノート

反応式

HRID 651437 の反応式
C(OC([N:11]1[C:16](=[O:17])[CH2:15][CH2:14][C:13]([NH2:19])([CH3:18])[C:12]1=[O:20])=O)C1C=CC=CC=1.[ClH:21].[H][H].O>C(O)C.[Pd]>[ClH:21].[NH2:19][C:13]1([CH3:18])[CH2:14][CH2:15][C:16](=[O:17])[NH:11][C:12]1=[O:20]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 21928242N-Benzyloxycarbonyl-alpha-amino-alpha-methylglutarimideHCID 178418361HCID 178418361、化合物

生成物 1

HCID 219282523-Amino-3-methylpiperidine-2,6-dione hydrochloride収率 93%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒2 回

実験手順

N-Benzyloxycarbonyl-α-amino-α-methylglutarimide (2.3 g, 8.3 mmol) was dissolved in ethanol (200 mL) with gentle heat and the resulting solution allowed to cool to room temperature. To this solution was added 4N hydrochloric acid (3 mL) followed by 10% Pd/C (0.4 g). The mixture was hydrogenated in a Parr apparatus under 50 psi of hydrogen for 3 hours. To the mixture was added water (50 mL) to dissolve the product. This mixture was filtered through a Celite pad which was washed with water (50 mL). The filtrate was concentrated in vacuo to afford a solid residue. The solid was slurried in ethanol (20 mL) for 30 min. The slurry was filtered to afford 1.38 g (93%) of α-amino-α-methylglutarimide hydrochloride as a white solid: 1H NMR (DMSO-d6) δ11.25 (s, 1H), 8.92 (s, 3H), 2.84-2.51 (m, 2H), 2.35-2.09 (m, 2H), 1.53 (s, 3H); HPLC, Waters Nova-Pak C18 column, 4 micron, 1 mL/min, 240 nm, 20/80 CH3CN/0.1% H3PO4(aq), 1.03 min (94.6%).

後処理

  1. temperaturewith gentle heat
  2. dissolutionto dissolve the product
  3. filtrationThis mixture was filtered through a Celite pad which
  4. washwas washed with water (50 mL)
  5. concentrationThe filtrate was concentrated in vacuo
  6. customto afford a solid residue
  7. filtrationThe slurry was filtered

出典と根拠

ORDレコード
ord-e0982250641c44f3930e175b38dd5b27
出典データセット
uspto-grants-2001_08
特許番号
US06281230B1

反応ノート

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