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

HRID 451881ノート

反応式

HRID 451881 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 59201744HCID 59201744、化合物

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-fb2593e68b4b4804a3a44069bb14db83
出典データセット
uspto-grants-2013_07
特許番号
US08487108B2

反応ノート

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