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

HRID 1015524노트

반응식

HRID 1015524 반응식
[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

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매2회HCID 312751,4-Dioxane용매2회

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-b5c0471d00c94f29abb142149b274e5d
출처 데이터셋
uspto-grants-2011_07
특허 번호
US07985759B2

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