Triethylsilane → (3R,5R,6S,7S)-7-(Benzyloxymethyl)-6-(4-fluorophenyl)-3-(-2-methoxy-5-(trifluoromethyl)phenyl)-1-oxaspiro[4.4]nonane

HRID 1417549Notes

Reaction equation

HRID 1417549 reaction equation
[CH2:1]([O:8][CH2:9][C@H:10]1[CH2:31][CH2:30][C@:12]2([O:16][CH2:15][C@@:14](O)([C:17]3[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][C:18]=3[O:27][CH3:28])[CH2:13]2)[C@@H:11]1[C:32]1[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([SiH](CC)CC)C>FC(F)(F)C(O)=O.C(OCC)(=O)C>[CH2:1]([O:8][CH2:9][C@H:10]1[CH2:31][CH2:30][C@:12]2([O:16][CH2:15][C@@H:14]([C:17]3[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][C:18]=3[O:27][CH3:28])[CH2:13]2)[C@@H:11]1[C:32]1[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 57132321HCID 57132321, compound

Product 1

HCID 21308075(3R,5R,6S,7S)-7-(Benzyloxymethyl)-6-(4-fluorophenyl)-3-(-2-methoxy-5-(trifluoromethyl)phenyl)-1-oxaspiro[4.4]nonaneYield 24.5%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution was prepared by dissolving 10 mg (0.019 mmol) of (3S,5R,6S,7S)-7-(benzyloxymethyl)-6-(4-fluorophenyl)-3-hydroxy-3-(2-methoxy-5-(trifluoromethyl)phenyl)-1-oxaspiro[4.4]nonane in 0.20 mL of trifluoroacetic acid at RT, and triethylsilane (0.009 mL, 7 mg, 0.06 mmol) was added immediately. After 30 min., the reaction was diluted with 25 mL of ethyl acetate and washed with 5 m L of saturated aqueous sodium bicarbonate and 5 mL of saturated aqueous sodium chloride. The organic solution was dried over sodium sulfate, decanted, and evaporated. The crude product was purified by preparative TLC, eluting with 3% ethyl ether in toluene, to yield 2.4 mg of the title compound.

Workup

  1. customA solution was prepared
  2. washwashed with 5 m L of saturated aqueous sodium bicarbonate and 5 mL of saturated aqueous sodium chloride
  3. dry with materialThe organic solution was dried over sodium sulfate
  4. customdecanted
  5. customevaporated
  6. customThe crude product was purified by preparative TLC
  7. washeluting with 3% ethyl ether in toluene

Sources & evidence

ORD record
ord-9aa8d92b0c87451fabbc41550d0bc42e
Source dataset
uspto-grants-1999_03
Patent number
US05877191

Reaction notes

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