Fluoride Ion → HCID 178465491, compound

HRID 2307178Notes

Reaction equation

HRID 2307178 reaction equation
[CH2:1]([NH:3][C:4](=[O:34])[O:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][Si](C(C)(C)C)(C)C)=[CH:14][C:13]=2[O:26][Si](C(C)(C)C)(C)C)[CH2:8][CH2:7]1)[CH3:2].[F-]>CO>[CH2:1]([NH:3][C:4](=[O:34])[O:5][C@H:6]1[CH2:11][CH2:10][C@H:9]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:13]=2[OH:26])[CH2:8][CH2:7]1)[CH3:2]

Participants

4

Reactant 2

HCID 28179Fluoride IonHCID 178465492HCID 178465492, compound

Product 1

HCID 178465491HCID 178465491, compoundYield 242.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of trans-4-(2,4-bis{[tert-butyl(dimethyl)silyl]oxy}phenyl)cyclohexyl ethylcarbamate (18 mg), methanol (10 ml) and Amberlyst fluoride resin (0.3 g) were stirred at room temperature for 24 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 (24 mg, 87%). δH(CD3OD) 1.10 (3H, t), 1.40-1.60 (4H, m), 1.80-1.90 (2H, m), 2.00-2.10 (2H, m), 2.72-2.80 (1H, m), 3.10 (2H, t), 4.50-4.60 (1H, m), 6.20-6.26 (2H, m), 6.88 (1H, d); m/z (ES+) 280 (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-1cc9b547ec9a43e0b1d722fa8b0d9e00
Source dataset
uspto-grants-2004_12
Patent number
US06828460B2

Reaction notes

Loading…