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

HRID 1157375ノート

反応式

HRID 1157375 の反応式
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

参加物

5

反応物 2

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

生成物 1

HCID 219309983-(Aminomethyl)piperidine-1-carboxamide収率 87.3%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒2 回HCID 312751,4-Dioxane溶媒

反応条件

温度
25 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-1f1222da5cc64907bec2ace4fda3cbc4
出典データセット
uspto-grants-2010_10
特許番号
US07807683B2

反応ノート

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