Acetic Acid → 1-(2-Oxopyrrolidin-1-yl)tricyclo[3.3.1.03,7]nonane-3-carboxylic acid

HRID 1015524Notes

Reaction equation

HRID 1015524 reaction equation
[OH-].[Na+].BrBr.Br[O-].[C:7]([C:10]12[CH2:17][CH:16]3[CH2:18][C:12]([N:19]4[CH2:23][CH2:22][CH2:21][C:20]4=[O:24])([CH2:13][CH:14]1[CH2:15]3)[CH2:11]2)(=[O:9])C.C(O)(=[O:27])C>O1CCOCC1.O>[O:24]=[C:20]1[CH2:21][CH2:22][CH2:23][N:19]1[C:12]12[CH2:18][CH:16]3[CH2:15][CH:14]([CH2:13]1)[C:10]([C:7]([OH:9])=[O:27])([CH2:17]3)[CH2:11]2

Participants

8

Reactant 5

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 24408BromineHCID 5460626HypobromiteHCID 673004661-(3-Acetyltricyclo[3.3.1.03,7]non-1-yl)pyrrolidin-2-one

Product 1

HCID 673007541-(2-Oxopyrrolidin-1-yl)tricyclo[3.3.1.03,7]nonane-3-carboxylic acidYield 129.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

To a stirred mixture of NaOH (2.4 g, 60.6 mmol), H2O (16 mL) and 1,4 dioxane (4 mL) at ice bath temperature was added Br2 (1.13 mL, 22.6 mmol) and stirred for 5 minutes. The resulting hypobromite solution was added dropwise to a stirred solution of the compound obtained in step I (1.0 g, 4.04 mmol) in 1,4-dioxane (18 mL) at 10° C. The temperature of the reaction was brought to room temperature and the reaction mixture was stirred for 1 h. Then it was cooled to ice bath temperature and quenched by adding acetic acid (3.9 mL, 65.7 mmol). The reaction mixture was diluted with water, extracted with EtOAc, and the combined organic layers were washed with brine and dried over Na2SO4. The solvent was removed under reduced pressure to obtain 1-(2-oxopyrrolidin-1-yl)tricyclo[3.3.1.03,7]nonane-3-carboxylic acid as a viscous liquid (1.3 g) in 100% yield. m/z (M+1) 250; 1H NMR (CDCl3) 300 MHz δ 3.42 (t, J=7.0 Hz, 2H), 2.78-2.71 (m, 1H), 2.47-2.23 (m, 6H), 2.08-1.90 (m, 6H), 1.85-1.72 (m, 2H), 1.62 (dd, J=2.4, 11.0 Hz, 1H).

Workup

  1. customwas brought to room temperature
  2. stirringthe reaction mixture was stirred for 1 h
  3. temperatureThen it was cooled to ice bath temperature
  4. customquenched
  5. extractionextracted with EtOAc
  6. washthe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b5c0471d00c94f29abb142149b274e5d
Source dataset
uspto-grants-2011_07
Patent number
US07985759B2

Reaction notes

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