HCID 58124946, compound → HCID 58124797, compound

HRID 1971697Notes

Reaction equation

HRID 1971697 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][C:12]([N:15]([CH3:23])[C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:14])[CH3:13])(C(C)(C)C)(C)C>[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1.[NH4+].[Cl-]>[OH:8][CH2:9][CH2:10][CH2:11][C:12]([N:15]([CH3:23])[C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:14])[CH3:13]

Participants

5

Reactant 1

HCID 58124946HCID 58124946, compound

Product 1

HCID 58124797HCID 58124797, compound

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 25517Ammonium ChlorideSolventHCID 2724141Tetrabutylammonium FluorideSolvent

Procedure

A solution of 550 mg of 12c in 4 ml of 1M tetra-n-butyl ammonium fluoride in THF was stirred at RT for 1 h. The reaction mixture was diluted with 25 ml of 5% aq. NH4Cl and the product was extracted with ethyl acetate. The organic layer was washed twice with sat. aq. NaCl, dried and concentrated. The crude material was purified by chromatography over silica gel, using a gradient of dichloromethane/ethyl acetate gradient as eluent. This provide 250 mg of 12d as a colorless oil. Rf 0.25 (CH2Cl2-ethyl acetate 8/2); MS-ESI: [M+1] 232.3, NMR (CDCl3) δ 1.32 (s, 6, 2×CH3), 1.48 (s, 9, tertC4H9), 1.55 (m, 2, CH2), 1.88 (m, 2, CH2), 2.88 (s, 3, NCH3), 3.02 (m, 2, CH2).

Workup

  1. extractionthe product was extracted with ethyl acetate
  2. washThe organic layer was washed twice with sat. aq. NaCl
  3. customdried
  4. concentrationconcentrated
  5. customThe crude material was purified by chromatography over silica gel

Sources & evidence

ORD record
ord-4a9d72494e4d41b0b17993b495ccf8ad
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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