4-(5-Chloro-2,3-dihydrofuro[2,3-c]pyridin-2-yl)piperidine-1-carboxylic acid tert-butyl ester → 4-[5-(2-Oxo-2H-pyrazin-1-yl)-2,3-dihydro-furo[2,3-c]pyridin-2-yl]-piperidine-1-carboxylic acid tert-butyl ester

HRID 1184766Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]2[O:23][C:17]3=[CH:18][N:19]=[C:20](Cl)[CH:21]=[C:16]3[CH2:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH:24][C:25]1[CH:30]=[N:29][CH:28]=[CH:27][N:26]=1>O1CCOCC1.[Cu](I)I>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([CH:14]2[O:23][C:17]3=[CH:18][N:19]=[C:20]([N:26]4[CH:27]=[CH:28][N:29]=[CH:30][C:25]4=[O:24])[CH:21]=[C:16]3[CH2:15]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of 4-(5-chloro-2,3-dihydro-furo[2,3-c]pyridin-2-yl)-piperidine-1-carboxylic acid tert-butyl ester (60 mg), 2-hydroxypyrazine (17 mg), and copper iodide (7 mg) in 1,4-dioxan (1 mL) is sparged with argon. N,N′-Dimethylethylendiamine (8.54) and tri-potassium orthophosphate (72 mg) are added and the resulting mixture is heated in a microwave oven to 180° C. for 1 h. The reaction mixture is filtered and chromatographed on silica gel (ethyl acetate) to give the title compound. LC (method 7): tR=1.32 min; Mass spectrum (ESI+): m/z=399 [M+H]+.

Workup

customis sparged with argon
additionN,N′-Dimethylethylendiamine (8.54) and tri-potassium orthophosphate (72 mg) are added
filtrationThe reaction mixture is filtered
customchromatographed on silica gel (ethyl acetate)

Sources & evidence

ORD record: ord-74f46fc3a9d344ff9a09f8b1f59f01d2
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08669271B2

Reaction notes

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