1-Phenyl-1,3,8-triazaspiro(4.5)decan-4-one → HCID 12150152, compound

HRID 1827277Notes

Reaction equation

HRID 1827277 reaction equation
[CH:1]1([O:11][C:12]2[CH:19]=[CH:18][C:15]([CH:16]=O)=[CH:14][CH:13]=2)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH2:3][CH2:2]1.[C:20]1([N:26]2[C:30]3([CH2:35][CH2:34][NH:33][CH2:32][CH2:31]3)[C:29](=[O:36])[NH:28][CH2:27]2)[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[C:20]1([N:26]2[C:30]3([CH2:31][CH2:32][N:33]([CH2:16][C:15]4[CH:18]=[CH:19][C:12]([O:11][CH:1]5[C:10]6[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=6)[CH2:4][CH2:3][CH2:2]5)=[CH:13][CH:14]=4)[CH2:34][CH2:35]3)[C:29](=[O:36])[NH:28][CH2:27]2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 705561-Phenyl-1,3,8-triazaspiro(4.5)decan-4-oneHCID 5049666Sodium triacetoxyborohydrideHCID 12150151HCID 12150151, compound

Product 1

HCID 12150152HCID 12150152, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a mixture of 4-(1,2,3,4-tetrahydro-1-naphthyloxy)benzaldehyde (264 mg, 1.05 mmol) and 1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one (232 mg, 1.00 mmol) in 1,2-dichloroethane (15 mL) was added sodium triacetoxyborohydride (369 mg, 1.74 mmol). The resultant reaction mixture was stirred at room temperature under argon atmosphere for 20 h. The reaction mixture was quenched with 1N aqueous NaHCO3 and extracted with CHCl3 (2×50 mL). The organic phase was dried over Na2SO4, filtered and concentrated. The crude product was purified by flash chromatography on silica gel (4% MeOH in CHCl3) to yield the title product as an off-white solid.

Workup

  1. customThe resultant reaction mixture
  2. customThe reaction mixture was quenched with 1N aqueous NaHCO3
  3. extractionextracted with CHCl3 (2×50 mL)
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by flash chromatography on silica gel (4% MeOH in CHCl3)

Sources & evidence

ORD record
ord-d2b302c8364f4c33b3ec6c1cee718dc6
Source dataset
uspto-grants-2006_05
Patent number
US07053101B2

Reaction notes

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