Triethylamine → HCID 15646116, compound

HRID 1655273

Reaction equation

HRID 1655273 reaction equation
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]

Participants

8

Reactant 3

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

Product 1

HCID 15646116HCID 15646116, compoundYield 76.1%

Reagents, catalysts & solvents 4

HCID 11430Potassium CarbonateCatalystHCID 313Hydrochloric AcidSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-5ebd17a7ebf543f2aa6fdad6211aef7d
Source dataset
uspto-grants-1993_10
Patent number
US05250537

Linked notes

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