Diisopropylethylamine → (1R)-Camphoric anhydride

HRID 1358592

Reaction equation

HRID 1358592 reaction equation
CCN(C(C)C)C(C)C.[C:10]([OH:23])(=[O:22])[C@@:11]1([CH2:21][CH2:20][C@H:16]([C:17]([OH:19])=O)[C:13]1([CH3:15])[CH3:14])[CH3:12].CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F>C1COCC1>[C:10]1(=[O:22])[O:23][C:17](=[O:19])[CH:16]2[CH2:20][CH2:21][C@@:11]1([C:13]2([CH3:14])[CH3:15])[CH3:12]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 101807Camphoric AcidHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphate

Product 1

HCID 68989(1R)-Camphoric anhydrideYield 90.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DIEA (8.0 g) was added to a suspension of (1R,3S)-camphoric acid (5.0 g) and BOP Reagent (11.1 g) in THF (50 ml) at room temperature. The mixture was stirred for 4 hr. and the solvent was removed in vacuo. The residue was extracted with AcOEt and the extract was washed with 5% HCl, sat. NaHCO3, and sat. LiCl, and dried over Na2SO4. The solvent was removed in vacuo and the residue was purified by flash chromatography on silica gel (eluent; CHCl3) to give (1R)-camphoric anhydride (4.1 g) as a colorless powder.

Workup

  1. customand the solvent was removed in vacuo
  2. extractionThe residue was extracted with AcOEt
  3. washthe extract was washed with 5% HCl, sat. NaHCO3, and sat. LiCl
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by flash chromatography on silica gel (eluent; CHCl3)

Sources & evidence

ORD record
ord-ce57b0fcec4a4611860b0c3e7d8dc83b
Source dataset
uspto-grants-2003_07
Patent number
US06596752B1

Linked notes

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