Acetic Acid → HCID 57481588, compound

HRID 1497649Notes

Reaction equation

[NH:1]1[CH2:6][CH2:5][CH:4]([C:7]([NH2:9])=[O:8])[CH2:3][CH2:2]1.CO.[C:12](O)(=O)[CH3:13].[C:16]([BH3-])#N.[Na+]>>[CH:13]1([N:1]2[CH2:6][CH2:5][CH:4]([C:7]([NH2:9])=[O:8])[CH2:3][CH2:2]2)[CH2:12][CH2:16]1

Participants

Reactant 4

HCID 176Acetic Acid

HCID 887Methanol

HCID 37724-Piperidinecarboxamide

HCID 5003444Sodium cyanoborohydride

Product 1

HCID 57481588HCID 57481588, compoundYield 121.9%

Conditions

Temperature: 60 °C

Procedure

To a solution of piperidine-4-carboxamide (1 g, 7.8 mmol) in MeOH (80 mL) 1-ethoxy-1-trimethylsilyloxycyclopropane (2.35 mL, 11.7 mmol, 1.5 eq) was added, followed by acetic acid (1.34 mL, 23.4 mmol, 3 eq) and sodium cyanoborohydride (923 mg, 12.48 mmol, 1.6 eq) and the mixture was stirred at 60° C. overnight. The solvent was then concentrated under reduced pressure and the residue was purified by flash chromatography on silica gel (DCM/MeOH/NH3 7 N in MeOH 90:9:1) affording 1.6 g of 1-cyclopropylpiperidine-4-carboxamide.

Workup

concentrationThe solvent was then concentrated under reduced pressure
customthe residue was purified by flash chromatography on silica gel (DCM/MeOH/NH3 7 N in MeOH 90:9:1)

Sources & evidence

ORD record: ord-13bf607ad4974d2e8a0c93d2dab8b891
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09199979B2

Reaction notes

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