Trifluoroacetic acid → HCID 60123707, compound

HRID 348400Notes

Reaction equation

HRID 348400 reaction equation
[CH:1]1([C:4](=[O:7])[CH:5]=[CH2:6])[CH2:3][CH2:2]1.C(O[CH2:13][N:14]([CH2:23][Si](C)(C)C)[C@@H:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH3:16])CCC.FC(F)(F)C(O)=O>ClC(Cl)C>[C:17]1([C@H:15]([N:14]2[CH2:13][CH2:6][CH:5]([C:4]([CH:1]3[CH2:3][CH2:2]3)=[O:7])[CH2:23]2)[CH3:16])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 5349541-Cyclopropyl-2-propen-1-oneHCID 15701915HCID 15701915, compound

Product 1

HCID 60123707HCID 60123707, compoundYield 49.6%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

In dry dichloroethane (350 ml) was dissolved the product (8.01 g) containing 1-cyclopropyl-2-propen-1-one described in Reference Example 2-1 and N-(n-butoxymethyl)-N-[1-(R)-phenylethyl]trimethylsilylmethylamine (23.2 g, 79.9 mmol), followed by dropwise addition of trifluoroacetic acid (500 μl). After stirring at room temperature for 12 hours, the reaction solution was washed with saturated sodium bicarbonate (100 ml) and then saturated saline (100 ml). The solution was dried over anhydrous sodium sulfate and, after filtration, the filtrate was concentrated under reduced pressure. The resulting residue was subjected to flash silica gel chromatography to obtain the title compound (9.08 g, 49.6%) as a colorless oil from the fraction eluted with n-hexane/ethyl acetate=2/1. By the way, this product was obtained as a 1:1 diastereomer mixture.

Workup

  1. washthe reaction solution was washed with saturated sodium bicarbonate (100 ml)
  2. dry with materialThe solution was dried over anhydrous sodium sulfate
  3. filtrationafter filtration
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-0bd6811c0433446d8508b8f3309c2fbe
Source dataset
uspto-grants-2007_02
Patent number
US07176313B2

Reaction notes

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