2-Bromo-3-methoxypyridine → 2-(3-methoxy-2-pyridinyl)-5-phenylmethyl-(1S,4S)-2,5-diazabicyclo[2.2.1]-heptane

HRID 1031487Notes

Reaction equation

Br[C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:10]([N:17]1[CH2:22][C@@H:21]2[CH2:23][C@H:18]1[CH2:19][NH:20]2)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(Cl)Cl>[CH3:9][O:8][C:7]1[C:2]([N:20]2[CH2:19][C@@H:18]3[CH2:23][C@H:21]2[CH2:22][N:17]3[CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:3][CH:4]=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 2-bromo-3-methoxy pyridine (9.9 g) and (1S,4S)-N-benzyl-2,5-diazabicyclo[2.2.1]heptane (10.9 g) was heated at 100° C. in a Parr bomb for 67 h. The reaction mixture was cooled to 23° C., dissolved in CH2Cl2, extracted with 5% NaHCO3, and finally wit:h H2O. The organic layer was dried over K2CO3, filtered, and concentrated under reduced pressure. The crude oil was purified by silica gel chromatography (CH2Cl2 :MeOH; 96:4) to give the desired product (7.93 g, 51%).

Workup

temperatureThe reaction mixture was cooled to 23° C.
extractionextracted with 5% NaHCO3, and finally wit
dry with materialThe organic layer was dried over K2CO3
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude oil was purified by silica gel chromatography (CH2Cl2 :MeOH; 96:4)

Sources & evidence

ORD record: ord-c33d51057ad54739892d9bc674b95593
Source dataset: uspto-grants-1990_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04954502

Reaction notes

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