Sodium borohydride → (4-(Cyclopropyl(6-methoxypyridin-3-yl)methoxy)-3-methoxyphenyl)methanamine

HRID 706500Notes

Reaction equation

[CH:1]1([CH:4]([C:16]2[CH:17]=[N:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)[O:5][C:6]2[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][C:7]=2[O:14][CH3:15])[CH2:3][CH2:2]1.[BH4-].[Na+]>C(O)C.O.O.O.O.O.O.[Co](Cl)Cl>[CH:1]1([CH:4]([C:16]2[CH:17]=[N:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=2)[O:5][C:6]2[CH:13]=[CH:12][C:9]([CH2:10][NH2:11])=[CH:8][C:7]=2[O:14][CH3:15])[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred 0° C. solution of 4-(cyclopropyl(6-methoxypyridin-3-yl)methoxy)-3-methoxybenzonitrile (2.50 g, 8.06 mmol) in ethanol (20 mL) was added cobalt(II) chloride hexahydrate (2.20 g, 9.25 mmol) in small portions. The resulting mixture was allowed to stir at 0° C. After 30 min, the mixture was treated with sodium borohydride (1.80 g, 47.58 mmol) added in small portions. The mixture was allowed to warm to room temperature. After 30 min, the mixture was filtered through Celite, and the filtercake was washed with ethanol (20 mL). The filtrate was concentrated to provide 2.50 g (99%) of (4-(cyclopropyl(6-methoxypyridin-3-yl)methoxy)-3-methoxyphenyl)methanamine as a colorless oil.

Workup

additionadded in small portions
temperatureto warm to room temperature
waitAfter 30 min
filtrationthe mixture was filtered through Celite
washthe filtercake was washed with ethanol (20 mL)
concentrationThe filtrate was concentrated

Sources & evidence

ORD record: ord-44d5a051deca435cbeb3c4d4012ea9a5
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09174986B2

Reaction notes

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