1,4-Dioxa-8-azaspiro(4.5)decane → HCID 68982573, compound

HRID 493117Notes

Reaction equation

HRID 493117 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[C@@H:13]1[CH2:15][O:14]1.[O:16]1[C:20]2([CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)[O:19][CH2:18][CH2:17]1.[O-]S(C(F)(F)F)(=O)=O.[Yb+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O>ClCCl>[O:16]1[C:20]2([CH2:25][CH2:24][N:23]([CH2:15][C@@H:13]([C:6]3[C:5]4[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=4)[N:9]=[CH:8][CH:7]=3)[OH:14])[CH2:22][CH2:21]2)[O:19][CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 674351,4-Dioxa-8-azaspiro(4.5)decaneHCID 2733225Ytterbium triflateHCID 11275682HCID 11275682, compound

Product 1

HCID 68982573HCID 68982573, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[R]-2-(6-Methoxyquinolin-4-yl)oxirane (1b) (470 mg) and 1,4-dioxa-8-azaspiro-[4,5]-decane (0.33 ml) were dissolved in dry dichloromethane (5 ml) and ytterbium triflate (30 mol %) was added. The mixture was stirred for 6 hours, filtered through celite, evaporated and chromatographed on silica gel (dichloromethane then methanol-dichloromethane) to afford the title compound (690 mg).

Workup

  1. filtrationfiltered through celite
  2. customevaporated
  3. customchromatographed on silica gel (dichloromethane

Sources & evidence

ORD record
ord-0443a2d7c1c14a0d89a24d48f0a7e270
Source dataset
uspto-grants-2009_05
Patent number
US07534793B2

Reaction notes

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