Trifluoroacetic acid → HCID 60123707, compound

HRID 2417247Notes

Reaction equation

HRID 2417247 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>[CH:1]1([C:4]([CH:5]2[CH2:6][CH2:13][N:14]([C@@H:15]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH3:16])[CH2:23]2)=[O:7])[CH2:3][CH2:2]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

The product (8.01 g) containing 1-cyclopropyl-2-propen-1-one described in Reference Example 1 and N-(n-butoxymethyl)-N-[1-(R)-phenylethyl]trimethylsilylmethylamine (23.2 g, 79.9 mmol) were dissolved in dry dichloroethane (350 ml), and trifluoroacetic acid (500 μl) was added dropwise thereto. After 12 hours of stirring at room temperature, the reaction solution was washed with saturated sodium bicarbonate aqueous solution (100 ml) and then with saturated brine (100 ml). After drying over anhydrous magnesium sulfate and subsequent filtration, the filtrate was concentrated under a reduced pressure. The thus obtained residue was subjected to a flash silica gel chromatography, and 9.08 g (49.6%) of the title compound was obtained from an eluate of n-hexane:ethyl acetate=2:1 as a colorless oil component. In this case, this product was obtained as a diastereomer mixture of 1:1.

Workup

  1. washthe reaction solution was washed with saturated sodium bicarbonate aqueous solution (100 ml)
  2. dry with materialAfter drying over anhydrous magnesium sulfate and subsequent filtration
  3. concentrationthe filtrate was concentrated under a reduced pressure

Sources & evidence

ORD record
ord-7d68d503ae144eac908e61abce0acc0c
Source dataset
uspto-grants-2004_11
Patent number
US06825353B2

Reaction notes

Loading…