Tetrahydrofuran → (3S,7aR)-6,6-Dibenzyl-3-tert-butyl-1,6,7,7a-tetrahydro-5-oxopyrrolo[1,2-c]oxazole-7a-carboxylic Acid Methyl Ester

HRID 1359174노트

반응식

HRID 1359174 반응식
[CH3:1][O:2][C:3]([C@:5]12[CH2:16][CH2:15][C:14](=[O:17])[N:6]1[C@H:7]([C:10]([CH3:13])([CH3:12])[CH3:11])[O:8][CH2:9]2)=[O:4].[Li+].[CH3:19][CH:20]([N-]C(C)C)[CH3:21].CN(P(N(C)C)(N(C)C)=O)C.BrCCC[CH:41]([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)C1C=CC=CC=1.[CH2:54]1[CH2:58]O[CH2:56][CH2:55]1>>[CH3:1][O:2][C:3]([C@:5]12[CH2:16][C:15]([CH2:41][C:48]3[CH:49]=[CH:50][CH:51]=[CH:52][CH:53]=3)([CH2:56][C:55]3[CH:21]=[CH:20][CH:19]=[CH:58][CH:54]=3)[C:14](=[O:17])[N:6]1[C@H:7]([C:10]([CH3:13])([CH3:12])[CH3:11])[O:8][CH2:9]2)=[O:4]

참가 물질

6

반응물 5

HCID 8028Tetrahydrofuran2회HCID 12679HexamethylphosphoramideHCID 2724682Lithium diisopropylamideHCID 11053798(3S,7aR)-3-tert-Butyl-1,6,7,7a-tetrahydro-5-oxopyrrolo[1,2-c]oxazole-7a-carboxylic Acid Methyl Ester2회HCID 122234581,1-Diphenyl-4-bromobutane

생성물 1

HCID 11069859(3S,7aR)-6,6-Dibenzyl-3-tert-butyl-1,6,7,7a-tetrahydro-5-oxopyrrolo[1,2-c]oxazole-7a-carboxylic Acid Methyl Ester

실험 절차

To a solution of bicycle 17 (260 mg, 1.08 mmol) in THF (7.0 mL) under nitrogen were added at −78° C. successively a solution of LDA (1.5 M, 1.0 mL) and HMPA (1.0 mL). After 1 h, 4-bromo-1,1-diphenylbutane (360 mg, 1.25 mmol) in THF (3.0 mL) was added. After 6 h at −78° C., the reaction mixture was quenched with saturated NH4Cl solution. The product was extracted into EtOAc, and the combined organic layers were washed with brine, dried (Na2SO4), and concentrated under reduced pressure. Separation by column chromatography (SiO2, hexane/EtOAc 30:1) afforded starting material 17 (140 mg, 54% recovery) and compound 14g (70 mg, 31%) besides traces of 14h (2 mg) and 14i (2 mg).

후처리

  1. waitAfter 6 h at −78° C.
  2. customthe reaction mixture was quenched with saturated NH4Cl solution
  3. extractionThe product was extracted into EtOAc
  4. washthe combined organic layers were washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated under reduced pressure
  7. customSeparation by column chromatography (SiO2, hexane/EtOAc 30:1)
  8. customafforded

출처 및 근거

ORD 기록
ord-d2c3645142db4131a886605b00405aeb
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06599940B2

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