Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)- → HCID 59201744, 화합물

HRID 451881노트

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HRID 451881 반응식
[CH2:1]1[C:3]2([CH2:8][CH2:7][C@H:6]([CH2:9][C@H:10]3[CH2:14][O:13]C(C)(C)[N:11]3[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:5][O:4]2)[CH2:2]1.C12(CS(O)(=O)=O)C(C)(C)C(CC1)CC2=O>CO>[CH2:2]1[C:3]2([CH2:8][CH2:7][C@H:6]([CH2:9][C@H:10]([NH:11][C:17](=[O:18])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])[CH2:14][OH:13])[CH2:5][O:4]2)[CH2:1]1

참가 물질

4

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HCID 18462Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-HCID 59201552HCID 59201552, 화합물

생성물 1

HCID 59201744HCID 59201744, 화합물

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

The (S)-tert-butyl 4-(((R)-4-oxaspiro[2.5]oct-6-yl)methyl)-2,2-dimethyloxazolidine-3-carboxylate (3.0 g, 9.17 mmol) and camphor sulphonic acid (2.2 g, 9.17 mmol, 1.0 equiv) were dissolved in 200 mL of MeOH and allowed to react at ambient temperature for 3 hr. The mixture was quenched with saturated NaHCO3 solution, the methanol removed in vacuo, and the mixture diluted with EtOAc. The layers were separated and the organic layer washed with brine, dried over Na2SO4, filtered and evaporated. This yielded 1.70 g (65%) of tert-butyl (S)-1-((R)-4-oxaspiro[2.5]oct-6-yl)-3-hydroxypropan-2-ylcarbamate which was used in the next step with no further purification. MS ESI +ve m/z 310 (M+Na).

후처리

  1. customto react at ambient temperature for 3 hr
  2. customThe mixture was quenched with saturated NaHCO3 solution
  3. customthe methanol removed in vacuo
  4. additionthe mixture diluted with EtOAc
  5. customThe layers were separated
  6. washthe organic layer washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated
  10. customThis yielded 1.70 g (65%) of tert-butyl (S)-1-((R)-4-oxaspiro[2.5]oct-6-yl)-3-hydroxypropan-2-ylcarbamate which was used in the next step with no further purification

출처 및 근거

ORD 기록
ord-fb2593e68b4b4804a3a44069bb14db83
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08487108B2

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