Diethylamine → HCID 53318597, compound

HRID 2042948Notes

Reaction equation

HRID 2042948 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@H:13]([OH:14])[C@@H:12]([OH:15])[C@H:11]([OH:16])[C@@H:10]([CH2:17]I)[O:9]2)=[CH:4][C:3]=1[CH2:19][C:20]1[S:21][C:22]([C:25]2[O:26][CH:27]=[CH:28][CH:29]=2)=[CH:23][N:24]=1.N(CC)CC>CO.[Ni]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@H:13]([OH:14])[C@@H:12]([OH:15])[C@H:11]([OH:16])[C@@H:10]([CH3:17])[O:9]2)=[CH:4][C:3]=1[CH2:19][C:20]1[S:21][C:22]([C:25]2[O:26][CH:27]=[CH:28][CH:29]=2)=[CH:23][N:24]=1

Participants

5

Reactant 2

HCID 8021DiethylamineHCID 86680892HCID 86680892, compound

Product 1

HCID 53318597HCID 53318597, compoundYield 31.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To the solution of iodide 95 (85 mg, 0.16 mmol) in methanol (1.6 mL) was added Et2NH (0.03 mL, 0.31 mmol) and Raney nickel (20 mg). The reaction mixture was stirred 1 d under H2 (1 atm), filtered on Celite and evaporated under reduced pressure. The residue was purified by prep HPLC (C18) to afford title compound 96 (21 mg, 31%) as a solid.

Workup

  1. filtrationfiltered on Celite
  2. customevaporated under reduced pressure
  3. customThe residue was purified by prep HPLC (C18)

Sources & evidence

ORD record
ord-e7f1d86d734747bfa1dee662b378e669
Source dataset
uspto-grants-2013_11
Patent number
US08586550B2

Reaction notes

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