3-Fluorobenzylamine → HCID 66960456, compound

HRID 1362649Notes

Reaction equation

HRID 1362649 reaction equation
[CH2:1]([O:3][C:4](=[O:26])/[C:5](=[CH:11]/[C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH:22]=[C:21]([CH3:23])[N:20]=[CH:19]2)=[C:14]([O:24][CH3:25])[CH:13]=1)/[CH2:6][CH2:7][CH2:8][CH:9]=O)[CH3:2].[F:27][C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=1)[CH2:31][NH2:32].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.C(O)(=O)C.C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:26])/[C:5](=[CH:11]/[C:12]1[CH:17]=[CH:16][C:15]([N:18]2[CH:22]=[C:21]([CH3:23])[N:20]=[CH:19]2)=[C:14]([O:24][CH3:25])[CH:13]=1)/[CH2:6][CH2:7][CH2:8][CH2:9][NH:32][CH2:31][C:30]1[CH:33]=[CH:34][CH:35]=[C:28]([F:27])[CH:29]=1)[CH3:2]

Participants

8

Reactant 4

HCID 668533-FluorobenzylamineHCID 5049666Sodium triacetoxyborohydrideHCID 86585896Sodium bicarbonate waterHCID 86602477HCID 86602477, compound

Product 1

HCID 66960456HCID 66960456, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a methylene chloride (6 mL) solution of (E)-2-(3-methoxy-4-(4-methyl-1H-imidazol-1-yl)benzylidene)-6-oxohexanoic acid ethyl ester (231 mg), 3-fluorobenzylamine (88.7 μL), acetic acid (0.5 mL) and sodium triacetoxy borohydride (165 mg) were added one by one. After agitating the reaction solution at room temperature overnight, a saturated sodium bicarbonate water and ethyl acetate were added to the reaction solution, and the organic layer was partitioned. After the obtained organic layer was washed with a saturated saline solution, it was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (Carrier: Chromatorex NH, elution solvent; heptane-ethyl acetate=1:1->ethyl acetate->ethyl acetate:ethanol=10:1), and 173 mg of the title compound was obtained. The physical properties of the compound are as follows.

Workup

  1. customthe organic layer was partitioned
  2. washAfter the obtained organic layer was washed with a saturated saline solution, it
  3. dry with materialwas dried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (Carrier: Chromatorex NH, elution solvent; heptane-ethyl acetate=1:1->ethyl acetate->ethyl acetate:ethanol=10:1)

Sources & evidence

ORD record
ord-7cd4c8f95f3f4df98ecc54408b0f94ac
Source dataset
uspto-grants-2011_02
Patent number
US07880009B2

Reaction notes

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