Reaction #48009

ord-3796f2cbad9f4ea3b625165eb0ec8225

Reaction equation

CS(=O)(=O)OC[C@@H]1CC2(C[C@@H]1COS(C)(=O)=O)OCCO2
methanesulfonic acid (7R,8S)-8-methanesulfonyloxymethyl-1,4-dioxaspiro-[4.4]non-7-ylmethyl ester
CCCCN
n-butylamine
→
CCCCN1C[C@@H]2CC3(C[C@@H]2C1)OCCO3
(3aR,6aS)-2-butylspiro[hexahydrocyclopenta[c]pyrrole-5(1H),2′-[1,3]dioxolane]

Reactants

CS(=O)(=O)OC[C@@H]1CC2(C[C@@H]1COS(C)(=O)=O)OCCO2
methanesulfonic acid (7R,8S)-8-methanesulfonyloxymethyl-1,4-dioxaspiro-[4.4]non-7-ylmethyl ester
CCCCN
n-butylamine

Reagents

None

Conditions

Temperature
90°CELSIUS
Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherThe reaction is evaporated
  2. 2
    Otherpartitioned between EtOAc and 2M aqueous NaOH
  3. 3
    WashThe organic phase is washed with brine
  4. 4
    Dryingdried (MgSO4)
  5. 5
    Otherevaporated
  6. 6
    OtherThe crude product is purified by flash chromatography
  7. 7
    Washeluting with EtOAc

Procedure

A suspension of methanesulfonic acid (7R,8S)-8-methanesulfonyloxymethyl-1,4-dioxaspiro-[4.4]non-7-ylmethyl ester (0.250 g, 0.73 mmol) in n-butylamine (1 ml) is heated at 90° C. for 3 hours. The reaction is evaporated and partitioned between EtOAc and 2M aqueous NaOH. The organic phase is washed with brine, dried (MgSO4) and evaporated. The crude product is purified by flash chromatography, eluting with EtOAc to afford (3aR,6aS)-2-butylspiro[hexahydrocyclopenta[c]pyrrole-5(1H),2′-[1,3]dioxolane], M+226.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07745462B2uspto-grants-2010_06