HCID 11694753, compound → HCID 57803517, compound

HRID 2103032Notes

Reaction equation

HRID 2103032 reaction equation
[CH3:1][O:2][NH:3][CH2:4][C:5]1[C:14]2([CH2:17][CH2:16][CH2:15]2)[O:13][C:12]2[C:7](=[C:8]([CH3:20])[C:9]([OH:19])=[C:10]([CH3:18])[CH:11]=2)[CH:6]=1>C(OCC)(=O)C.[Pd]>[CH3:1][O:2][NH:3][CH2:4][CH:5]1[C:14]2([CH2:15][CH2:16][CH2:17]2)[O:13][C:12]2[C:7](=[C:8]([CH3:20])[C:9]([OH:19])=[C:10]([CH3:18])[CH:11]=2)[CH2:6]1

Participants

4

Reactant 1

HCID 11694753HCID 11694753, compound

Product 1

HCID 57803517HCID 57803517, compoundYield 17.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-[(methoxyamino)methyl]-5,7-dimethylspiro[chromene-2,1′-cyclobutan]-6-ol (300 mg) in 20 mL of ethyl acetate was treated with Pd (100 mg, 10% on activated carbon), flushed with H2, and left stirring in a hydrogen atmosphere overnight. After filtration through a pad of silica, the solvents were evaporated. The residue was purified by flash chromatography eluted with 30% ethyl acetate and hexane to give 54.0 mg of 3-[(methoxyamino)methyl]-5,7-dimethyl-3,4-dihydrospiro[chromene-2,1′-cyclobutan]-6-ol as an off-white solid. 1H-NMR (300 MHz, CDCl3) δ=6.51 (s, 1H), 3.57 (s, 3H), 2.20 (s, 3H), 2.13 (s, 3H), 3.20-1.50 (m, 11H) ppm. 13C-NMR (75 MHz, CDCl3) δ=146.5, 145.9, 122.6, 122.4, 117.7, 116.3, 79.2, 62.0, 50.5, 35.4, 33.5, 31.7, 23.3, 16.2, 12.8, 11.6 ppm. MS: (m/z)=278.2 (M+H+).

Workup

  1. customflushed with H2
  2. waitleft
  3. filtrationAfter filtration through a pad of silica
  4. customthe solvents were evaporated
  5. customThe residue was purified by flash chromatography
  6. washeluted with 30% ethyl acetate and hexane

Sources & evidence

ORD record
ord-71580cd040c149e59b59810750cc47c5
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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