Triethylamine → HCID 15646116, 화합물

HRID 1655273

반응식

HRID 1655273 반응식
C[N:2]1[CH:7]2[CH2:8][C:9]([CH2:11][CH:3]1[CH2:4][CH2:5][CH2:6]2)=[O:10].[Cl:12][C:13]([Cl:20])([Cl:19])[CH2:14][O:15][C:16](Cl)=[O:17].C(N(CC)CC)C>C1(C)C=CC=CC=1.C(OCC)(=O)C.Cl.C(=O)([O-])[O-].[K+].[K+]>[Cl:12][C:13]([Cl:20])([Cl:19])[CH2:14][O:15][C:16]([N:2]1[CH:7]2[CH2:6][CH2:5][CH2:4][CH:3]1[CH2:11][C:9](=[O:10])[CH2:8]2)=[O:17]

참가 물질

8

반응물 3

HCID 8471TriethylamineHCID 11096psi-PelletierineHCID 870632,2,2-Trichloroethyl chloroformate

생성물 1

HCID 15646116HCID 15646116, 화합물수율 76.1%

시약·촉매·용매 4

HCID 11430Potassium Carbonate촉매HCID 313Hydrochloric Acid용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of pseudopelletierine (52 g, 0.34 mol) in toluene (220 mL) at 50° C. was added anhydrous potassium carbonate (1.0 g), followed by the slow addition of trichloroethylchloroformate (79 g, 0.37 mol). After addition was completed (30 minutes), triethylamine (10 mL) was added. The reaction was allowed to cool to room temperature and stirred for 18 hours. The reaction mixture was diluted with ethyl acetate (300 mL) and 1N hydrochloric acid (200 mL). After the organic layer was washed with 1N hydrochloric acid (100 mL), it was washed with aqueous 10% sodium hydroxide (100 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated to afford a beige solid which was triturated with hexane (300 mL) to afford 81.4 g of crystalline solid (76% yield); mp 95°-96° C. after recrystallization from ethyl acetate-hexane. Anal. (C11H14C13NO3).

후처리

  1. additionAfter addition
  2. additionwas added
  3. washAfter the organic layer was washed with 1N hydrochloric acid (100 mL), it
  4. washwas washed with aqueous 10% sodium hydroxide (100 mL)
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford a beige solid which
  9. customwas triturated with hexane (300 mL)

출처 및 근거

ORD 기록
ord-5ebd17a7ebf543f2aa6fdad6211aef7d
출처 데이터셋
uspto-grants-1993_10
특허 번호
US05250537

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