Triethylsilane → HCID 56974282, compound

HRID 1417557Notes

Reaction equation

HRID 1417557 reaction equation
C([SiH](CC)CC)C.[CH3:8][O:9][C:10]([C@H:12]1[CH2:37][CH2:36][C@:14]2([O:18][CH:17]=[C:16]([C:19]3[CH:24]=[C:23]([N:25]4[CH:29]=[CH:28][N:27]=[C:26]4[C:30]([F:33])([F:32])[F:31])[CH:22]=[CH:21][C:20]=3[O:34][CH3:35])[CH2:15]2)[C@@H:13]1[C:38]1[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=1)=[O:11]>FC(F)(F)C(O)=O>[CH3:8][O:9][C:10]([C@H:12]1[CH2:37][CH2:36][C@:14]2([O:18][CH2:17][C@H:16]([C:19]3[CH:24]=[C:23]([N:25]4[CH:29]=[CH:28][N:27]=[C:26]4[C:30]([F:31])([F:32])[F:33])[CH:22]=[CH:21][C:20]=3[O:34][CH3:35])[CH2:15]2)[C@@H:13]1[C:38]1[CH:39]=[CH:40][C:41]([F:44])=[CH:42][CH:43]=1)=[O:11].[CH3:8][O:9][C:10]([C@H:12]1[CH2:37][CH2:36][C@:14]2([O:18][CH2:17][C@@H:16]([C:19]3[CH:24]=[C:23]([N:25]4[CH:29]=[CH:28][N:27]=[C:26]4[C:30]([F:31])([F:32])[F:33])[CH:22]=[CH:21][C:20]=3[O:34][CH3:35])[CH2:15]2)[C@@H:13]1[C:38]1[CH:39]=[CH:40][C:41]([F:44])=[CH:42][CH:43]=1)=[O:11]

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 67670838HCID 67670838, compound

Product 2

HCID 56974282HCID 56974282, compoundHCID 67670401HCID 67670401, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Triethylsilane (0.0062 mL, 4.5 mg, 0.039 mmol) was added to a solution of (5R,6S,7S)-6-(4-fluorophenyl)-3-(2-methoxy-5-(2-(trifluoromethyl)imidazol-1-yl)phenyl)-1-oxaspiro[4.4]non-2-ene-7-carboxylic acid methyl ester (6.8 mg, 0.013 mmol) in 0.204 mL of trifluoroacetic acid at RT. The mixture was stirred 1 h at RT, then overnight at 60° C. After removing the solvent under reduced pressure, the residue was dissolved in 3.0 mL of ethyl acetate, washed with 2.0 mL of saturated aqueous sodium bicarbonate, dried over sodium sulfate and evaporated. The crude product was purified by preparative TLC, eluting twice with 3% ethyl ether in dichloromethane, to give 1.0 mg of (3S,5R,6S,7S)-6-(4-fluorophenyl)-3-(2-methoxy-5-(2-(trifluoromethyl)imidazol-1-yl)phenyl)-1-oxaspiro[4.4]nonane-7-carboxylic acid methyl ester and 2.6 mg of the title compound. 1NMR (400 MHz, CDCl3): δ 7.37 (dd, 2H, J=9, 6 Hz ), 7.19 (d, 1H, J=1 Hz), 7.15 (dd, 1H, J=9, 3 Hz ), 7.09 (d, 1H, J=2 Hz ), 7.08 (d, 1H, J=1 Hz ), 7.03 (t, 2H, J=9 Hz ), 6.82 (1H, J=9 Hz ), 3.78 (s, 3H), 3.70 (t, 1H, J=8 Hz ), 3.62 (t, 1H, J=8 Hz ), 3.56 (s, 3H), 3.14 (ddd, 1H, J=11, 10, 7 Hz ), 3.12 (d, 1H, J=11 Hz ), 2.87 (quintet, 1H, J=8 Hz ), 2.33-2.23 (m, 2H), 2.08-1.88 (m, 4H). Mass spectrum (ESI): m/z=519 (M+1).

Workup

  1. customovernight
  2. customat 60° C
  3. customAfter removing the solvent under reduced pressure
  4. dissolutionthe residue was dissolved in 3.0 mL of ethyl acetate
  5. washwashed with 2.0 mL of saturated aqueous sodium bicarbonate
  6. dry with materialdried over sodium sulfate
  7. customevaporated
  8. customThe crude product was purified by preparative TLC
  9. washeluting twice with 3% ethyl ether in dichloromethane

Sources & evidence

ORD record
ord-cb7fdc7d2abc400eba347b001ab32efa
Source dataset
uspto-grants-1999_03
Patent number
US05877191

Reaction notes

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