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

HRID 548945
Notes
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Reaction equation

HRID 548945 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 119845943,9-Diazaspiro[5.5]undecane, 3-(6-methoxy-2-naphthalenyl)-

Product 1

HCID 159408093-(6-Methoxynaphthalen-2-yl)-9-methyl-3,9-diazaspiro[5.5]undecaneYield 87.6%

Reagents, catalysts & solvents 1

HCID 63651,1-Dichloroethane
Solvent

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

  1. stirringstirred at room temperature over night
  2. customThe reaction was quenched with aqueous sodium hydrogencarbonate (sat.)
  3. customevaporated
  4. extractionThe remaining aqueous phase was extracted three times with dichloromethane
  5. dry with materialthe combined organic phase was dried (sodium sulfate)
  6. filtrationfiltered
  7. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes