Hydrochloric Acid → HCID 11694753, compound

HRID 2103031Notes

Reaction equation

HRID 2103031 reaction equation
[CH3:1][O:2][N:3]=[CH: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.Cl>C1COCC1.O1CCOCC1>[CH3:1][O:2][NH:3][CH2:4][C: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)[CH:6]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 72998856HCID 72998856, compound

Product 1

HCID 11694753HCID 11694753, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 6-hydroxy-5,7-dimethylspiro[chromene-2,1′-cyclobutane]-3-carbaldehyde O-methyloxime (150 mg) in 10 mL of THF at 0° C. was added BH3/pyridine complex (2.27 mL). Subsequently, 9 mL of HCl in dioxane (4.0 M solution) was added over a period of 1 hour. The reaction mixture was allowed to stir overnight. The mixture was extracted with ethyl acetate, washed with saturated NaHCO3, and concentrated in vacuo. The residue was purified by flash chromatography eluted with 30% ethyl acetate in hexane to give 142 mg of 3-[(methoxyamino)methyl]-5,7-dimethylspiro[chromene-2,1′-cyclobutan]-6-ol as a yellow solid. 1H-NMR (300 MHz, CDCl3) δ=6.59 (s, 1H, =CH), 6.45 (s, 1H), 5.50 (b, 1H), 4.75 (b, 1H), 3.81 (s, 2H), 3.62 (s, 3H), 2.20 (s, 3H), 2.19 (s, 3H), 2.40-1.75 (m, 6H) ppm. 13C-NMR (75 MHz, CDCl3) δ=146.3, 146.0, 134.0, 123.9, 120.3, 119.4, 119.1, 114.6, 81.1, 62.0, 54.7, 33.1, 16.5, 14.3, 11.2 ppm. MS: (m/z)=229.1 (M−NH2OMe+).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washwashed with saturated NaHCO3
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash chromatography
  5. washeluted with 30% ethyl acetate in hexane

Sources & evidence

ORD record
ord-df431042dddc488a8514630abf27f471
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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