HCID 86644996, compound → HCID 67003850, compound

HRID 1045242Notes

Reaction equation

HRID 1045242 reaction equation
[CH2:1]([O:8][C@H:9]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH:33]([CH3:35])[CH3:34])[CH2:10][C:11]([O:13]CC(C1C=CC(Br)=CC=1)=O)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)(=O)C.C(Cl)Cl.[Zn]>[CH2:1]([O:8][C@H:9]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH:33]([CH3:35])[CH3:34])[CH2:10][C:11]([OH:13])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 86644996HCID 86644996, compound

Product 1

HCID 67003850HCID 67003850, compoundYield 97%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

Zinc dust (<10 micron, 382 mg, 5.87 mmol) was added portionwise to a solution of 117 (320 mg, 0.587 mmol) in acetic acid (15 mL). The reaction mixture was stirred at 60° C. for 2 h and then diluted with DCM (20 mL). The solids were filtered off through a pad of Celite and the residue was washed with DCM (3×5 mL). The combined filtrates were concentrated in vacuo and the residue was purified by silica gel column chromatography (eluent: DCM/methanol, 100/1, v/v) to afford 107 as an amorphous solid (198 mg, 97%). Rf=0.40 (toluene/ethyl acetate, 3/1, v/v); [α]25D=−2.3° (c=1.0, CHCl3); 1H NMR (300 MHz, CDCl3): δ 7.35-7.25 (m, 5H, aromatic), 4.55 (s, 2H, CH2Ph), 3.86 (m, 1H, H-3), 2.62 (dd, 1H, J2a,2b=15.6 Hz, J2a,3=6.9 Hz, H-2a), 2.53 (dd, 1H, J2a,2b=15.6 Hz, J2b,3=5.1 Hz, H-2b), 1.66-1.45 (m, 3H, H-4, H-13), 1.38-1.10 [m, 16H, H-(5-12)], 0.85 (d, 6H, J15,16=6.9 Hz, H-14); 13C NMR (75 MHz, CDCl3): δ 176.76 (C═O), 138.04-127.73 (aromatic), 75.70 (C-3), 71.53 (CH2Ph), 39.42 (C-2), 39.03 (C-12), 34.09 (C-4), 22.66 (C-14); HR MS (m/z) calculated for C22H36O3 [M Na]+, 371.2557; found, 371.1906.

Workup

  1. filtrationThe solids were filtered off through a pad of Celite
  2. washthe residue was washed with DCM (3×5 mL)
  3. concentrationThe combined filtrates were concentrated in vacuo
  4. customthe residue was purified by silica gel column chromatography (eluent

Sources & evidence

ORD record
ord-be1ee4ab9c4b48618e9a113742140aeb
Source dataset
uspto-grants-2013_10
Patent number
US08563523B2

Reaction notes

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