Acetic Acid → Methyl 3-aminopiperidine-1-carboxylate

HRID 2212180노트

반응식

HRID 2212180 반응식
C(O)(=O)C.Cl.[CH3:6][O:7][C:8]([N:10]1[CH2:15][CH2:14][CH2:13][CH:12]([NH:16]C(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:11]1)=[O:9]>C(#N)C>[CH3:6][O:7][C:8]([N:10]1[CH2:15][CH2:14][CH2:13][CH:12]([NH2:16])[CH2:11]1)=[O:9]

참가 물질

5

반응물 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 696524093-(Trityl-amino)-piperidine-1-carboxylic acid methyl ester

생성물 1

HCID 22273098Methyl 3-aminopiperidine-1-carboxylate수율 95.6%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

Add acetic acid saturated with HCl(g) (100 mL, ˜3N in HCl) to 3-(trityl-amino)-piperidine-1-carboxylic acid methyl ester (6.51 g, 16.2 mmol). Stir the solution vigorously at room temperature for 2 hours. Concentrate the reaction, follow this by addition of acetonitrile and concentration to assist in the removal of acetic acid (×2). Partition the resulting material between 1N HCl and ethyl acetate, separate the layers, extract the organic layer with 1N HCl. Basify the combined aqueous layers with 5N sodium hydroxide, extract with 20% isopropanol/chloroform (×3). Dry the combined organic layers over magnesium sulfate and concentrate to give 2.45 g of the title compound as a white solid, 95% yield. 1H NMR: consistent with structure. MS (ion spray) 158 (M+).

후처리

  1. concentrationConcentrate
  2. customthe reaction
  3. customto assist in the removal of acetic acid (×2)
  4. customPartition the resulting material between 1N HCl and ethyl acetate
  5. customseparate the layers
  6. extractionextract the organic layer with 1N HCl
  7. extractionextract with 20% isopropanol/chloroform (×3)
  8. dry with materialDry the combined organic layers over magnesium sulfate
  9. concentrationconcentrate

출처 및 근거

ORD 기록
ord-8d411f7d4713493f87e38178998d2b8d
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07101891B2

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