1,4-Dioxa-8-azaspiro(4.5)decane → HCID 22293841, compound

HRID 967361Notes

Reaction equation

HRID 967361 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH2:13][N:14]([C:17](=[O:19])[CH3:18])[CH2:15][CH2:16][C:11]=3[N:10]([CH2:20][CH:21]3[CH2:23][O:22]3)[N:9]=2)=[CH:4][CH:3]=1.[O:24]1[C:28]2([CH2:33][CH2:32][NH:31][CH2:30][CH2:29]2)[O:27][CH2:26][CH2:25]1.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.C(S([O-])(=O)=O)(F)(F)F.[Yb+3].O>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]3[CH2:13][N:14]([C:17](=[O:19])[CH3:18])[CH2:15][CH2:16][C:11]=3[N:10]([CH2:20][CH:21]([OH:22])[CH2:23][N:31]3[CH2:32][CH2:33][C:28]4([O:27][CH2:26][CH2:25][O:24]4)[CH2:29][CH2:30]3)[N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 11221240HCID 11221240, compoundHCID 45075687Ytterbium(3+) trifluoromethanesulfonate--water (1/3/1)

Product 1

HCID 22293841HCID 22293841, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 3.20 g (9.64 mmol) of 1-[3-(4-chloro-phenyl)-1-oxiranylmethyl-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridin-5-yl]-ethanone and 2.07 g (14.5 mmol) of 1,4-dioxa-8-azaspiro[4.5]decane in CH2Cl2 (65 mL) was added 1.79 g (2.89 mmol) of Yb(OTf)3.H2O. The reaction was stirred overnight and was then directly purified by flash chromatography (silica, 0-5% MeOH/CH2Cl2) to afford 3.70 g (81%) of the title compound. TLC (silica, 5% MeOH/CH2Cl2): Rf=0.35. MS (electrospray), m/z calculated for C24H31ClN4O4 [M++H], 475.20, observed 475.1.

Workup

  1. customwas then directly purified by flash chromatography (silica, 0-5% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-02b8024b44b64b298d17c202f03bec22
Source dataset
uspto-grants-2005_10
Patent number
US06953793B2

Reaction notes

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