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

HRID 1453945

反応式

HRID 1453945 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-95d16f1e44ab42759a9ac01222834064
出典データセット
uspto-grants-2009_01
特許番号
US07476665B2

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