Fluoride Ion → HCID 178521994, compound

HRID 585718Notes

Reaction equation

HRID 585718 reaction equation
[CH:1]1([NH:7][C:8](=[O:38])[O:9][C@H:10]2[CH2:15][CH2:14][C@H:13]([C:16]3[CH:21]=[CH:20][C:19]([O:22][Si](C(C)(C)C)(C)C)=[CH:18][C:17]=3[O:30][Si](C(C)(C)C)(C)C)[CH2:12][CH2:11]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[F-]>CO>[CH:1]1([NH:7][C:8](=[O:38])[O:9][C@H:10]2[CH2:11][CH2:12][C@H:13]([C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][C:17]=3[OH:30])[CH2:14][CH2:15]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 28179Fluoride IonHCID 178455062HCID 178455062, compound

Product 1

HCID 178521994HCID 178521994, compoundYield 36.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of trans-4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexyl cyclohexylcarbamate (28 mg), methanol (10 ml) and Amberlyst fluoride resin (0.3 g) were stirred at room temperature for 72 hr. The reaction mixture was filtered and the filtrate was evaporated in vacuo. The residue was purified by flash column chromatography (SiO2, ethyl acetate/petrol, 1:3 v/v) to give the title compound as a white solid (6 mg, 36%); δH (CD3OD) 1.10-2.12 (18H, m), 2.70-2.82 (1H, m), 4.46-4.60 (1H, m), 6.18-6.30 (2H, m), 6.80-6.92 (1H, m); m/z (ES+) 334 (M+H)+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe filtrate was evaporated in vacuo
  3. customThe residue was purified by flash column chromatography (SiO2, ethyl acetate/petrol, 1:3 v/v)

Sources & evidence

ORD record
ord-17f2fadf66c84c12a4ddee4ac73d3264
Source dataset
uspto-grants-2005_08
Patent number
US06933319B2

Reaction notes

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