4-Methoxybenzylamine → HCID 66799287, compound

HRID 1193321Notes

Reaction equation

[CH3:1][C:2]1([CH3:16])[C:7](=O)[CH2:6][CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3]1.[CH3:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH2:24])=[CH:21][CH:20]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCl>[CH3:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH:24][CH:7]2[CH2:6][CH2:5][N:4]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:3][C:2]2([CH3:16])[CH3:1])=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 0 °C

Procedure

tert-Butyl 3,3-dimethyl-4-oxopiperidine-1-carboxylate (3.3 g, 14.53 mmol, 1 eq) and 4-methoxybenzylamine (3.98 g, 29.07 mmol, 2 eq) were dissolved in dichloromethane (40 ml), and stirring was carried out for 2 h at RT. The reaction mixture was cooled to 0° C., and Na(OAc)3BH (9.24 g, 43.61 mmol, 3 eq) was added in portions. Then stirring was carried out for 16 h at RT. The reaction mixture was diluted with dichloromethane (150 ml), washed with water and sat. NaCl solution (in each case 100 ml), dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by column chromatography (Alox neutral, 10% ethyl acetate in hexane) (colourless oil). Yield: 38% (1.948 g, 5.59 mmol).

Workup

stirringThen stirring
waitwas carried out for 16 h at RT
washwashed with water and sat. NaCl solution (in each case 100 ml),
dry with materialdried over sodium sulfate
concentrationconcentrated under reduced pressure
customThe crude product was purified by column chromatography (Alox neutral, 10% ethyl acetate in hexane) (colourless oil)

Sources & evidence

ORD record: ord-fec72004c5f94bbca02947cd85f09a09
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08680159B2

Reaction notes

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