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

HRID 651437노트

반응식

HRID 651437 반응식
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]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 21928242N-Benzyloxycarbonyl-alpha-amino-alpha-methylglutarimideHCID 178418361HCID 178418361, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매2회

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-e0982250641c44f3930e175b38dd5b27
출처 데이터셋
uspto-grants-2001_08
특허 번호
US06281230B1

반응 노트

불러오는 중…