Potassium Carbonate → HCID 86684711, compound

HRID 339208Notes

Reaction equation

HRID 339208 reaction equation
[C@]12(C)C(C)(C)C(CC1)CC2C([O:12][C@H:13]([C:18]1[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[CH:20][C:19]=1[N+:26]([O-:28])=[O:27])[C:14]([CH3:17])([CH3:16])[CH3:15])=O.C([O-])([O-])=O.[K+].[K+]>CO>[CH3:25][O:24][C:22]1[CH:21]=[CH:20][C:19]([N+:26]([O-:28])=[O:27])=[C:18]([C@@H:13]([OH:12])[C:14]([CH3:17])([CH3:16])[CH3:15])[CH:23]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86684712HCID 86684712, compound

Product 1

HCID 86684711HCID 86684711, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of (S)-1-(5-methoxy-2-nitrophenyl)-2,2-dimethyl-1-propyl (1S)-camphanate (590 mg, 1.4 mmol) and K2CO3 (389 mg, 2.8 mmol) in methanol (MeOH, 25 mL) was heated to reflux for one hour, then cooled down, concentrated in vacuo, and diluted with CH2Cl2 (50 mL). The organic phase was washed with brine (50 mL), dried over Na2SO4, concentrated in vacuo, and the residue was purified by silica gel column chromatography to yield enantiopure (S)-1-(5-methoxy-2-nitrophenyl)-2,2-dimethyl-1-propanol (333 mg, 99%). 1H NMR was identical with that of the racemic alcohol.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for one hour
  3. temperaturecooled down
  4. concentrationconcentrated in vacuo
  5. additiondiluted with CH2Cl2 (50 mL)
  6. washThe organic phase was washed with brine (50 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo
  9. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-f4a1e62f9dfd4a5cbc657fbd882c82fd
Source dataset
uspto-grants-2014_11
Patent number
US08889860B2

Reaction notes

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