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

HRID 451881Notes

Reaction equation

HRID 451881 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 59201744HCID 59201744, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-fb2593e68b4b4804a3a44069bb14db83
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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