Piperidine → HCID 86638530, compound

HRID 1695244Notes

Reaction equation

HRID 1695244 reaction equation
[CH:1]([CH:3]1[CH2:5][CH:4]1[C:6]([O:8][CH2:9][CH3:10])=[O:7])=O.[NH:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH2:9]([O:8][C:6]([C@@H:4]1[CH2:5][C@H:3]1[CH2:1][N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:7])[CH3:10]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 89334Ethyl 2-formylcyclopropanecarboxylateHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 86638530HCID 86638530, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Under N2 atmosphere, ethyl 2-formyl-1-cyclopropanecarboxylate (3.0 g, 21.1 mmol, 1.2 eq) and piperidine (1.5 g, 17.6 mmol, 1.0 eq) were dissolved in DCM (45 mL); after 2 hours at room temperature, the mixture was cooled at 0° C. and sodium triacetoxyborohydride (5.6 g, 26.4 mmol, 1.5 eq) was added dropwise. The mixture was stirred at room temperature for 2.5 hours, then the organic phase was washed with NaOH aq and water to give 3.3 g of the title product (yield 89%).

Workup

  1. washthe organic phase was washed with NaOH aq and water

Sources & evidence

ORD record
ord-987c849ce8c9426f8bd66309c28a609e
Source dataset
uspto-grants-2012_04
Patent number
US08163729B2

Reaction notes

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