4-Fluoro-3-methylphenol → 1-Benzyl-3-[(4-fluoro-3-methylphenoxy)methyl]azepane

HRID 467471Notes

Reaction equation

HRID 467471 reaction equation
[CH2:1]([N:8]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]([CH2:15][OH:16])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][C:18]1[CH:19]=[C:20](O)[CH:21]=[CH:22][C:23]=1[F:24].CC(OC(/N=N/C(OC(C)C)=O)=O)C>C(Cl)Cl>[CH2:1]([N:8]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]([CH2:15][O:16][C:20]2[CH:21]=[CH:22][C:23]([F:24])=[C:18]([CH3:17])[CH:19]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 27373944-Fluoro-3-methylphenolHCID 5363146Diisopropyl azodicarboxylateHCID 21901990(1-Benzylazepan-3-yl)methanol

Product 1

HCID 584052701-Benzyl-3-[(4-fluoro-3-methylphenoxy)methyl]azepane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1-4 (500 mg, 2.280 mmol), 3-methyl-4-fluorophenol (288 mg, 2.280 mmol), and tiphenylphosphine-resin bound (1.060 g @ 2.15 mmol/g) in DCM (20 ml) was treated with DIAD (0.443 ml, 2.280 mmol). The mixture was stirred overnight at RT, filtered, and the filtrate was concentrated. The crude material was purified by gradient elution on silica gel (0 to 50% EtOAc in Hex) to yield 1-5 as a pale yellow oil. Data for 1-5: LRMS m/z (M+H): 328.2.

Workup

  1. filtrationfiltered
  2. concentrationthe filtrate was concentrated
  3. customThe crude material was purified by gradient elution on silica gel (0 to 50% EtOAc in Hex)

Sources & evidence

ORD record
ord-e31dac045d7c4a0998fd8a96c21d602b
Source dataset
uspto-grants-2014_01
Patent number
US08623863B2

Reaction notes

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