Formaldehyde → 3-(6-Methoxynaphthalen-2-yl)-9-methyl-3,9-diazaspiro[5.5]undecane

HRID 548945Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([N:13]1[CH2:18][CH2:17][C:16]3([CH2:23][CH2:22][NH:21][CH2:20][CH2:19]3)[CH2:15][CH2:14]1)[CH:7]=[CH:6]2.C=O.[C:26](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[C:8]([N:13]1[CH2:18][CH2:17][C:16]3([CH2:23][CH2:22][N:21]([CH3:26])[CH2:20][CH2:19]3)[CH2:15][CH2:14]1)[CH:7]=[CH:6]2

Participants

Conditions

Temperature: 0 °C

Procedure

To an ice cooled solution of 3-(6-methoxy-naphthalen-2-yl)-3,9-diaza-spiro[5.5]-undecane (294 mg, 0.95 mmol) in dichloroethane (20 mL), formaldehyde (37% in water, 204 μL, 2.84 mmol) was added and stirred for 1 h at 0° C. Sodium triacetoxyborohydride (402 mg, 1.89 mmol) was added and stirred at room temperature over night. The reaction was quenched with aqueous sodium hydrogencarbonate (sat.) and evaporated. The remaining aqueous phase was extracted three times with dichloromethane and the combined organic phase was dried (sodium sulfate), filtered and evaporated to give 270 mg (80%) of 3-(6-methoxy-naphthalen-2-yl)-9-methyl-3,9-diaza-spiro[5.5]undecane. Mp. 122.2-124.9° C.

Workup

stirringstirred at room temperature over night
customThe reaction was quenched with aqueous sodium hydrogencarbonate (sat.)
customevaporated
extractionThe remaining aqueous phase was extracted three times with dichloromethane
dry with materialthe combined organic phase was dried (sodium sulfate)
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-58911322213c41249ed7ef5c398f4cd4
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07943630B2

Reaction notes

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