Acetic Acid → Ethyl 4-[({3-[(tert-butoxycarbonyl)amino]pyridin-4-yl}methyl)amino]piperidine-1-carboxylate

HRID 271896

反応式

HRID 271896 の反応式
[C:1](O[BH-](OC(=O)C)OC(=O)C)(=O)[CH3:2].[Na+].C(O)(=O)C.[C:19]([N:26]1C=CC(C=O)=[C:28]([NH2:34])[CH2:27]1)([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].[NH2:35][CH:36]1[CH2:41][CH2:40][N:39]([C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH2:38][CH2:37]1.Cl[CH:48](Cl)[CH3:49]>>[C:22]([O:21][C:19]([NH:26][C:27]1[CH:28]=[N:34][CH:1]=[CH:2][C:48]=1[CH2:49][NH:35][CH:36]1[CH2:37][CH2:38][N:39]([C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH2:40][CH2:41]1)=[O:20])([CH3:23])([CH3:24])[CH3:25]

参加物

6

反応物 5

HCID 176Acetic AcidHCID 63651,1-DichloroethaneHCID 100867Ethyl 4-amino-1-piperidinecarboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 70700445N-Boc-3-amino-4-pyridine carboxaldehyde

生成物 1

HCID 22293284Ethyl 4-[({3-[(tert-butoxycarbonyl)amino]pyridin-4-yl}methyl)amino]piperidine-1-carboxylate

実験手順

Sodium triacetoxyborohydride (0.57 g, 2.70 mmol) and acetic acid (0.41, 6.75 mmol) were added to a solution of N-Boc-3-amino-4-pyridine carboxaldehyde (0.50 g, 2.25 mmol) and ethyl 4-aminopiperidine-1-carboxylate (0.47 g, 2.70 mmol) in dichloroethane (5 mL)at room temperature. The reaction was stirred overnight, and quenched with saturated aqueous sodium bicarbonate. This was separated, extracted with ethyl acetate and the combined organics were dried over sodium sulfate. The solution was filtered and evaporated to give the crude product. This was purified by chromatography (silica gel, 1 to 12% methanol in methylene chloride gradient elution), which gave the title compound (0.47 g). MS 379.3.

後処理

  1. customquenched with saturated aqueous sodium bicarbonate
  2. customThis was separated
  3. extractionextracted with ethyl acetate
  4. dry with materialthe combined organics were dried over sodium sulfate
  5. filtrationThe solution was filtered
  6. customevaporated
  7. customto give the crude product
  8. customThis was purified by chromatography (silica gel, 1 to 12% methanol in methylene chloride gradient elution), which

出典と根拠

ORDレコード
ord-233eb01d14024e7cadda9caf4190c3c1
出典データセット
uspto-grants-2008_11
特許番号
US07452903B2

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