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

HRID 1417549노트

반응식

HRID 1417549 반응식
[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

참가 물질

5

반응물 2

HCID 12052TriethylsilaneHCID 57132321HCID 57132321, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 6422Trifluoroacetic acid용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9aa8d92b0c87451fabbc41550d0bc42e
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05877191

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