Reaction equation
[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]Participants
6
Reactant 5
Product 1
Procedure
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.
Workup
- customquenched with saturated aqueous sodium bicarbonate
- customThis was separated
- extractionextracted with ethyl acetate
- dry with materialthe combined organics were dried over sodium sulfate
- filtrationThe solution was filtered
- customevaporated
- customto give the crude product
- customThis was purified by chromatography (silica gel, 1 to 12% methanol in methylene chloride gradient elution), which
Sources & evidence
- ORD record
- ord-5b0200ddee62494ca6d44f8890ce8d26
- Source dataset
- uspto-grants-2005_10
- Patent number
- US06953790B2
Linked notes
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