HCID 66614869, compound → HCID 58571264, compound

HRID 2046040Notes

Reaction equation

HRID 2046040 reaction equation
CC1(C)[O:7][CH2:6][C:5]([C:9]#[C:10][C:11]2[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[CH:13][CH:12]=2)([OH:8])[CH2:4][O:3]1>C(O)(C(F)(F)F)=O.CCO.[Pd]>[CH2:17]([C:14]1[CH:15]=[CH:16][C:11]([CH2:10][CH2:9][C:5]([OH:8])([CH2:6][OH:7])[CH2:4][OH:3])=[CH:12][CH:13]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24]

Participants

5

Reactant 1

HCID 66614869HCID 66614869, compound

Product 1

HCID 58571264HCID 58571264, compoundYield 100.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of the product of Step B (0.03 g; 0.087 mmol) and 10% Pd/C (0.05 g) in 5% TFA in EtOH (10 ml) was stirred for 1 h under H2 (balloon) at room temperature, then filtered through a pad of Celite, washed with CH2Cl2 (2×10 ml). To combined filtrates were evaporated to dryness under reduced pressure and dried in vacuo for 1 h to give title compound (0.027 g; 99%) as a colourless solid. 1H-NMR (CDCl3) 7.05 (s, 4H); 3.66 (broad m, 7H); 2.61 (m, 2H); 2.51 (t, 2H, J=7.92 Hz); 1.73 (m 2H); 1.55 (t, 3H, J=6.93 Hz); 1.26 (m, 10H); 0.87 (t, 3H, J=6.93 Hz).

Workup

  1. filtrationfiltered through a pad of Celite
  2. washwashed with CH2Cl2 (2×10 ml)
  3. customwere evaporated to dryness under reduced pressure
  4. customdried in vacuo for 1 h

Sources & evidence

ORD record
ord-0bc5896e6fd340c08e17fcca46de8205
Source dataset
uspto-grants-2013_11
Patent number
US08592399B2

Reaction notes

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