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

HRID 1768192Notes

Reaction equation

HRID 1768192 reaction equation
[C:1](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C.[C:19]([N:26]1[CH:31]=[CH:30][C:29]([NH2:32])=C(C=O)C1)([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:31]1[CH:30]=[CH:29][N:32]=[CH:1][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]

Participants

6

Reactant 5

HCID 176Acetic AcidHCID 63651,1-DichloroethaneHCID 100867Ethyl 4-amino-1-piperidinecarboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 20848820N-Boc4-amino-3-pyridine carboxaldehyde

Product 1

HCID 22293255Ethyl 4-[(4-[(tert-butoxycarbonyl)amino]pyridin-3-yl methyl)amino]piperidine-1-carboxylate

Procedure

Sodium triacetoxyborohydride (1.70 g, 8.03 mmol) and acetic acid (0.29, 4.82 mmol) were added to a solution of N-Boc-4-amino-3-pyridine carboxaldehyde (0.36 g, 1.61 mmol) and ethyl 4-aminopiperidine-1-carboxylate (0.33 g, 1.93 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, 0 to 12% methanol in methylene chloride gradient elution), which gave the title compound (0.24 g). MS 379.2.

Workup

  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, 0 to 12% methanol in methylene chloride gradient elution), which

Sources & evidence

ORD record
ord-5ce57c3cda794f038f311fa3e1e48b39
Source dataset
uspto-grants-2007_06
Patent number
US07235545B2

Reaction notes

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