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

HRID 451881Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 451881
[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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 59201744HCID 59201744, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-fb2593e68b4b4804a3a44069bb14db83
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08487108B2

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