Sodium cyanoborohydride → 2,6-Dichloro-4-(1-(oxetan-3-yl)piperidin-4-yl)pyridine

HRID 1778183Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([CH:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:5]=[C:4]([Cl:14])[N:3]=1.[O:15]1[CH2:18][C:17](=O)[CH2:16]1.C([BH3-])#N.[Na+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([CH:8]2[CH2:9][CH2:10][N:11]([CH:17]3[CH2:18][O:15][CH2:16]3)[CH2:12][CH2:13]2)[CH:5]=[C:4]([Cl:14])[N:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

A solution of 2,6-dichloro-4-(piperidin-4-yl)pyridine (2 g, 8.7 mmol) and oxetan-3-one (6.26 g, 87 mmol) in THF (50 mL) was stirred at 70° C. for 30 min and then sodium cyanoborohydride (2.74 g, 43.5 mmol) was added to the mixture and the mixture solution was stirred at 70° C. for additional 30 min. The reaction solution was filtered and the filtrate was concentrated to give crude product which was purified by flash column chromatography on silica gel (30% ethyl acetate in petroleum ether) to afford 2,6-dichloro-4-(1-(oxetan-3-yl)piperidin-4-yl)pyridine. (2 g, 88.7% yield). LCMS (ESI) [MH]+=286.7.

Workup

filtrationThe reaction solution was filtered
concentrationthe filtrate was concentrated
customto give crude product which
customwas purified by flash column chromatography on silica gel (30% ethyl acetate in petroleum ether)

Sources & evidence

ORD record: ord-6f03b0cc1bda4fc793400460177804bd
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09266862B2

Reaction notes

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