HCID 178455336, compound → HCID 178516223, compound

HRID 1672725Notes

Reaction equation

HRID 1672725 reaction equation
C([Si](C)(C)[O:6][C@@H:7]1[CH2:12][CH2:11][C@H:10]([N:13]2[CH2:17][CH2:16][CH2:15][C:14]2=[O:18])[CH2:9][CH2:8]1)(C)(C)C>Cl.CCO>[OH:6][C@@H:7]1[CH2:8][CH2:9][C@H:10]([N:13]2[CH2:17][CH2:16][CH2:15][C:14]2=[O:18])[CH2:11][CH2:12]1

Participants

4

Reactant 1

HCID 178455336HCID 178455336, compound

Product 1

HCID 178516223HCID 178516223, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolvent

Procedure

Heat a solution of cis-1-[4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-pyrrolidin-2-one (500 mg) in 5 mL of 1N HCl in EtOH to 45° C. for 1 h. Cool the mixture to room temp and concentrate. Dissolve the residue in NaHCO3 (10 mL) and CH2Cl2 (10 mL). Extract the aqueous layer two times with 10 mL of CH2Cl2. Dry the organic layer over Na2SO4, filter and concentrate. Purify the crude material by chromatography to yield the title compound: mass spectrum (m/z): 184 (M+1).

Workup

  1. concentrationconcentrate
  2. dissolutionDissolve the residue in NaHCO3 (10 mL)
  3. extractionExtract the aqueous layer two times with 10 mL of CH2Cl2
  4. dry with materialDry the organic layer over Na2SO4
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify the crude material by chromatography

Sources & evidence

ORD record
ord-000a4b6bd78c49beaf6ba122a6f9a46f
Source dataset
uspto-grants-2011_08
Patent number
US07998999B2

Reaction notes

Loading…