Hydrochloric Acid → HCID 57803545, compound

HRID 2103037Notes

Reaction equation

HRID 2103037 reaction equation
[CH3:1][O:2][N:3]=[C:4]1[C:16]2[C:11](=[C:12]([CH3:21])[C:13]([CH3:20])=[C:14]([OH:19])[C:15]=2[CH2:17][CH3:18])[O:10][C:6]2([CH2:9][CH2:8][CH2:7]2)[CH2:5]1.Cl>C1COCC1.O1CCOCC1>[CH2:17]([C:15]1[C:14]([OH:19])=[C:13]([CH3:20])[C:12]([CH3:21])=[C:11]2[C:16]=1[CH:4]([NH:3][O:2][CH3:1])[CH2:5][C:6]1([O:10]2)[CH2:9][CH2:8][CH2:7]1)[CH3:18]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 76614995HCID 76614995, compound

Product 1

HCID 57803545HCID 57803545, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

5-Ethyl-6-hydroxy-7,8-dimethylspiro[chromene-2,1′-cyclobutan]-4(3H)-one O-methyloxime was dissolved in 10 mL of THF. To this solution at 0° C. was added BH3/pyrine complex (2.27 mL). Subsequently, a solution of 9 mL of HCl in dioxane (4.0 M) was added over a period of 1 hour. The reaction mixture was allowed to stir overnight. The mixture was extracted with ethyl acetate and washed with saturated NaHCO3. After evaporation of the solvents, the residue was purified by flash chromatography eluted with 5-8% ethyl acetate in hexane to give 136.4 mg of the product 5-ethyl-4-(methoxyamino)-7,8-dimethyl-3,4-dihydrospiro[chromene-2,1′-cyclobutan]-6-ol. 1H-NMR (300 MHz, CDCl3) δ=4.40 (b, 1H), 4.30 (m; 1H), 3.66 (s, 3H), 2.19 (s, 3H), 2.17 (s, 3H), 2.70-1.60 (m, 6H), 1.25 (t, 3H) ppm. 13C-NMR (75 MHz, CDCl3) δ=146.3, 145.2, 126.1, 124.1, 123.4, 114.1, 76.8, 61.8, 52.4, 36.0, 35.0, 32.9, 19.2, 14.9, 13.9, 13.4, 12.4 ppm. MS: (m/z)=245.1 (M−NH2OMe+).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. washwashed with saturated NaHCO3
  3. customAfter evaporation of the solvents
  4. customthe residue was purified by flash chromatography
  5. washeluted with 5-8% ethyl acetate in hexane

Sources & evidence

ORD record
ord-a9f87842ba6e4fe58ffe78dc91dd6729
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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