Formaldehyde → 9-(3,4-Dichlorophenoxy)-3-methyl-3-azaspiro[5.5]undecane

HRID 554478Notes

Reaction equation

C(O[C:6]([N:8]1[CH2:13][CH2:12][C:11]2([CH2:18][CH2:17][CH:16]([O:19][C:20]3[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=3)[CH2:15][CH2:14]2)[CH2:10][CH2:9]1)=O)(C)(C)C.C=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C>[Cl:27][C:22]1[CH:21]=[C:20]([CH:25]=[CH:24][C:23]=1[Cl:26])[O:19][CH:16]1[CH2:17][CH2:18][C:11]2([CH2:10][CH2:9][N:8]([CH3:6])[CH2:13][CH2:12]2)[CH2:14][CH2:15]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a ice cooled solution of 9-(3,4-dichloro-phenoxy)-3-aza-spiro[5.5]undecane-3-carboxylic acid tert-butyl ester (60 mg, 0.19 mmol) in dichloroethane (10 mL), formaldehyde (37% in water, 54 μL, 0.72 mmol) was added and stirred for 1 h at 0° C. Sodium triacetoxyborohydride (102 mg, 0.48 mmol) was added and stirred over night at room temperature. The reaction was quenched with aqueous sodium hydrogen-carbonate and evaporated. The remaining aqueous phase was extracted four times with dichloromethane and the combined organic phase was dried (sodium sulfate), filtered and evaporated to give 75 mg (95%) 9-(3,4-dichloro-phenoxy)-3-methyl-3-aza-spiro[5.5]undecane as a yellow oil. LC-ESI-HRMS of [M+H]+ shows 328.1249 Da. Calc. 328.123495 Da, dev. 4.3 ppm.

Workup

stirringstirred over night at room temperature
customThe reaction was quenched with aqueous sodium hydrogen-carbonate
customevaporated
extractionThe remaining aqueous phase was extracted four times with dichloromethane
dry with materialthe combined organic phase was dried (sodium sulfate)
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-1483b6f170ec499c830f703487d7716f
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08049012B2

Reaction notes

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