Potassium Hydroxide → 7-(5-Isobutylpyridin-2-yl)-7-azaspiro[3.5]non-2-ylamine

HRID 336560Notes

Reaction equation

[OH-].[K+].C(OC(=O)[NH:7][CH:8]1[CH2:11][C:10]2([CH2:16][CH2:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23][CH:24]([CH3:26])[CH3:25])=[CH:19][N:18]=3)[CH2:13][CH2:12]2)[CH2:9]1)C>C(O)C.O>[CH2:23]([C:20]1[CH:21]=[CH:22][C:17]([N:14]2[CH2:13][CH2:12][C:10]3([CH2:9][CH:8]([NH2:7])[CH2:11]3)[CH2:16][CH2:15]2)=[N:18][CH:19]=1)[CH:24]([CH3:26])[CH3:25]

Participants

Conditions

Temperature: 110 °C

Procedure

1.21 g (21.65 mmol) of potassium hydroxide are added, at room temperature, to a solution of 0.37 g (1.08 mmol) of ethyl[7-(5-isobutylpyridin-2-yl)-7-azaspiro[3.5]non-2-yl]carbamate in 5 mL of ethanol/water (1/1). The mixture is then heated at 110° C. for 15 hours. The resulting mixture is allowed to cool to room temperature and is then concentrated under reduced pressure. The reaction medium is taken up in saturated sodium chloride solution and dichloromethane, the aqueous phase is separated out and extracted with dichloromethane, and the combined organic phases are dried over sodium sulfate. After evaporating under reduced pressure and purifying on a column of silica gel, eluting with a 100/0/0 to 96/4/0.4 mixture of dichloromethane, methanol and 28% aqueous ammonia, 0.27 g of expected product is obtained in the form of a wax.

Workup

temperatureto cool to room temperature
concentrationis then concentrated under reduced pressure
customdichloromethane, the aqueous phase is separated out
extractionextracted with dichloromethane
dry with materialthe combined organic phases are dried over sodium sulfate
customAfter evaporating under reduced pressure
custompurifying on a column of silica gel
washeluting with a 100/0/0 to 96/4/0.4 mixture of dichloromethane, methanol and 28% aqueous ammonia

Sources & evidence

ORD record: ord-fa0f2117dd294b268580835c215fd460
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889702B2

Reaction notes

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