Sulfuric Acid → 3-(Aminomethyl)piperidine-1-carboxamide

HRID 2039560노트

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HRID 2039560 반응식
C(OC([NH:8][CH2:9][CH:10]1[CH2:15][CH2:14][CH2:13][N:12]([C:16]([NH2:18])=[O:17])[CH2:11]1)=O)(C)(C)C.S(=O)(=O)(O)O>CO.O1CCOCC1>[NH2:8][CH2:9][CH:10]1[CH2:15][CH2:14][CH2:13][N:12]([C:16]([NH2:18])=[O:17])[CH2:11]1

참가 물질

5

반응물 2

HCID 1118Sulfuric AcidHCID 219310003-(Tert-butoxycarbonylaminomethyl)piperidine-1-carboxamide

생성물 1

HCID 219309983-(Aminomethyl)piperidine-1-carboxamide수율 87.3%

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 312751,4-Dioxane용매

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온도
25 °C

실험 절차

3-(tert-Butoxycarbonylaminomethyl)piperidine-1-carboxamide (150 mg, 0.583 mmoles) (prepared as described in Preparative Example 241, Step A above) was dissolved in methanol (3 mL). 10% conc. sulfuric acid in 1,4-dioxane (7.9 mL) was added and the mixture was stirred at 25° C. for 1 h. The mixture was diluted with methanol and BioRad AG1-X8 resin (OH− form) was added until the pH was basic. The resin was filtered off, washed with methanol, evaporated to dryness and chromatographed on a silica gel column (15×2 cm) using dichloromethane followed by 15% (10% conc, ammonium hydroxide in methanol)-dichloromethane as the eluant to give the 3-(aminomethyl)piperidine-1-carboxamide (80 mg, 87%): FABMS: m/z 158.1 (MH+); HRFABMS: m/z 158.1294 (MH+). Calcd. for C7H16N3O: m/z 158.1293; δH (CDCl3+drop CD3OD) 1.20 (1H, m, CH2), 1.48 (1H, m, CH2), 1.60 (1H, m, CH), 1.68 (1H, m, CH2), 1.83 (1H, m, CH2), 2.64 (bm, 2H, —CH2NH2), 2.82 (1H, m, CH2), 3.02 (1H, m, CH2), 2.98 (2H, m, CH2), 3.70 (1H, m, —CH2NH2), 3.78 (1H, m, —CH2NH2) and 5.24 ppm (1H, bs, NH); δC (CDCl3+drop CD3OD) CH2: 24.1, 28.6, 44.0, 44.8, 47.9; CH: 38.3; C, 159.0.

후처리

  1. additionresin (OH− form) was added until the pH
  2. filtrationThe resin was filtered off
  3. washwashed with methanol
  4. customevaporated to dryness
  5. customchromatographed on a silica gel column (15×2 cm)

출처 및 근거

ORD 기록
ord-e66214c66ec141809ed33a1e6d95c853
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08580782B2

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