Sodium Bicarbonate → HCID 68006128, compound

HRID 1026533Notes

Reaction equation

[NH2:1][C:2]1[C:3]([O:9][C:10]2([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:12][CH2:11]2)=[N:4][CH:5]=[C:6]([Cl:8])[CH:7]=1.O=[C:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>ClCCCl>[C:16]([O:15][C:13]([C:10]1([O:9][C:3]2[C:2]([NH:1][CH:21]3[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]3)=[CH:7][C:6]([Cl:8])=[CH:5][N:4]=2)[CH2:12][CH2:11]1)=[O:14])([CH3:19])([CH3:18])[CH3:17]

Participants

Conditions

Temperature: 75 °C

Procedure

At room temperature, to a 1,2-dichloroethane solution (280 ml) of tert-butyl 1-[(3-amino-5-chloropyridin-2-yl)oxy]cyclopropanecarboxylate (7.88 g) were added tert-butyl 4-oxopiperidine-1-carboxylate (22.1 g) and sodium triacetoxyborohydride (23.5 g), and then temperature was raised to 75° C., followed by stirring for 20 hours. After the temperature was brought back to room temperature, a saturated aqueous sodium hydrogen carbonate solution was added, and extracted with dichloromethane. The collected organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to afford tert-butyl 4-[(2-{[1-(tert-butoxycarbonyl)cyclopropyl]oxy}-5-chloropyridin-3-yl)amino]piperidine-1-carboxylate (7.09 g).

Workup

customwas brought back to room temperature
extractionextracted with dichloromethane
dry with materialThe collected organic layer was dried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-1334ac7c91ef461e8cd141a6e331e340
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08729095B2

Reaction notes

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