Sodium Hydroxide → 2-[4-(Diethoxymethyl)benzyl]-8-isobutyl-2,8-diazaspiro[4.5]decane

HRID 2067721Notes

Reaction equation

HRID 2067721 reaction equation
[CH2:1]([N:5]1[CH2:14][CH2:13][C:8]2([CH2:12][NH:11][CH2:10][CH2:9]2)[CH2:7][CH2:6]1)[CH:2]([CH3:4])[CH3:3].[CH2:15]([O:17][CH:18]([O:27][CH2:28][CH3:29])[C:19]1[CH:26]=[CH:25][C:22]([CH:23]=O)=[CH:21][CH:20]=1)[CH3:16].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[OH-].[Na+]>C(O)(=O)C.CN(C)C=O>[CH2:28]([O:27][CH:18]([O:17][CH2:15][CH3:16])[C:19]1[CH:26]=[CH:25][C:22]([CH2:23][N:11]2[CH2:10][CH2:9][C:8]3([CH2:7][CH2:6][N:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[CH2:14][CH2:13]3)[CH2:12]2)=[CH:21][CH:20]=1)[CH3:29]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 5959934-(Diethoxymethyl)benzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 58026283HCID 58026283, compound

Product 1

HCID 689535472-[4-(Diethoxymethyl)benzyl]-8-isobutyl-2,8-diazaspiro[4.5]decaneYield 61.5%

Reagents, catalysts & solvents 1

HCID 21926011acetic acid N,N-dimethylformamideSolvent

Procedure

To a 10% acetic acid-dimethylformamide (10 mL) solution of 8-isobutyl-2,8-diazaspiro[4.5]decane (600 mg) and 4-(diethoxymethyl)benzaldehyde (661 mg), sodium triacetoxyborohydride (1.30 g) was added. The reaction solution was stirred at room temperature for 14 hours. To the reaction solution, an aqueous 5N sodium hydroxide solution (10 mL) was added. The aqueous layer was extracted twice with dichloromethane (20 mL). The combined organic layer was washed with saturated sodium chloride solution (20 mL) and then dried over anhydrous magnesium sulfate. After removing the anhydrous magnesium sulfate by filtration, the filtrate was concentrated. The residue was purified by silica gel chromatography (ethyl acetate:methanol: 28% aqueous ammonia=1:0:0→100:5:1→100:10:2) to obtain the title compound (730 mg) having the following physical properties.

Workup

  1. extractionThe aqueous layer was extracted twice with dichloromethane (20 mL)
  2. washThe combined organic layer was washed with saturated sodium chloride solution (20 mL)
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customAfter removing the anhydrous magnesium sulfate
  5. filtrationby filtration
  6. concentrationthe filtrate was concentrated
  7. customThe residue was purified by silica gel chromatography (ethyl acetate:methanol: 28% aqueous ammonia=1:0:0→100:5:1→100:10:2)

Sources & evidence

ORD record
ord-9f6d769491ca43cfa9de24b345e726c4
Source dataset
uspto-grants-2012_10
Patent number
US08293896B2

Reaction notes

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