Acetic Acid → tert-Butyl 4-[(propan-2-yl)amino]piperidine-1-carboxylate

HRID 591652ノート

反応式

HRID 591652 の反応式
O=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[CH:15]([NH2:18])([CH3:17])[CH3:16].C(O)(=O)C.C([BH3-])#N.[Na+]>CO>[CH:15]([NH:18][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1)([CH3:17])[CH3:16]

参加物

6

反応物 4

HCID 176Acetic AcidHCID 6363IsopropylamineHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 20801236tert-Butyl 4-[(propan-2-yl)amino]piperidine-1-carboxylate収率 41%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To the solution of tert-butyl 4-oxopiperidine-1-carboxylate (5.0 g, 25.09 mmol) in methanol (35 mL) was added isopropylamine (1.07 mL, 12.54 mmol), acetic acid (0.94 mL, 16.30 mmol) and sodium cyanoborohydride (1.0 g, 16.30 mmol). The resulting solution was stirred at room temperature for 1 hour, then quenched with water. The solution was concentrated in vacuo and redissolved in ethyl ether. The organics were extracted with 0.1 N HCl. The aqueous extracts were basified with 1 N NaOH (pH>8) and extracted with ethyl ether. The organic extracts were dried over anhydrous Na2SO4, filtered, and concentrated in vacuo, to afford tert-butyl 4-(isopropylamino)piperidine-1-carboxylate (1.2 g, 41%) as a clear liquid.

後処理

  1. customquenched with water
  2. concentrationThe solution was concentrated in vacuo
  3. dissolutionredissolved in ethyl ether
  4. extractionThe organics were extracted with 0.1 N HCl
  5. extractionextracted with ethyl ether
  6. dry with materialThe organic extracts were dried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-56d616bad1aa4c429cedc30b1da826fd
出典データセット
uspto-grants-2016_01
特許番号
US09238640B2

反応ノート

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