Potassium Hydroxide → 2287238-27-9

HRID 1257627

반응식

HRID 1257627 반응식
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

참가 물질

5

반응물 2

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

생성물 1

HCID 685920612287238-27-9수율 38%

시약·촉매·용매 2

HCID 887Methanol용매HCID 962Water용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-5543dab3bf9a45428089b861327a1e1d
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461328B2

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