Hydrochloric Acid → HCID 57803511, compound

HRID 2103045Notes

Reaction equation

HRID 2103045 reaction equation
C[O:2][N:3]=[C:4]1[C:16]2[C:11](=[CH:12][C:13]([CH2:19][CH3:20])=[C:14]([OH:18])[C:15]=2[CH3:17])[O:10][C:6]2([CH2:9][CH2:8][CH2:7]2)[CH2:5]1.Cl.O.O1CCOC[CH2:24]1>>[CH2:19]([C:13]1[CH:12]=[C:11]2[C:16]([CH:4]([N:3]([OH:2])[CH3:24])[CH2:5][C:6]3([O:10]2)[CH2:9][CH2:8][CH2:7]3)=[C:15]([CH3:17])[C:14]=1[OH:18])[CH3:20]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 312751,4-DioxaneHCID 86605490HCID 86605490, compound

Product 1

HCID 57803511HCID 57803511, compound

Procedure

To a mixture of 7-ethyl-6-hydroxy-5-methylspiro[chroman-2,1′-cyclobutan]-4-one O-methyl oxime (530 mg) and BH3 pyridine complex (8 M, 2 mL) at 0° C., was added a solution of HCl in dioxane (4 M, 8 mL) at 1.5 mL/h. The mixture was cooled with ice-water bath, water was added to quench it, and extracted with ethyl acetate. The organic layer was washed with water, dried, and evaporated. The residue was purified by silica gel column eluting with 10% ethyl acetate in hexane, giving 7-ethyl-4-(hydroxy(methyl)amino)-5-methylspiro[chroman-2,1′-cyclobutan]-6-ol as a clear oil (412 mg) 1H-NMR (300 MHz, CDCl3) δ=6.57 (s, 1H), 5.25 (br., 1H), 4.30 (s, 1H), 3.63 (s, 3H), 2.67 (m, 4H), 2.2-1.7 (m, 9H), 1.19 (t, J=7.5 Hz, 3H) ppm. 13C-NMR (75 MHz, CDCl3) δ=148.20, 145.41, 131.08, 122.82, 115.47, 114.99, 61.94, 52.60, 35.63, 34.36, 32.54, 23.14, 13.76, 13.66, 11.41 ppm. MS (m/z)=231 (100, M−N(OH)CH3).

Workup

  1. temperatureThe mixture was cooled with ice-water bath
  2. customto quench it
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water
  5. customdried
  6. customevaporated
  7. customThe residue was purified by silica gel column
  8. washeluting with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-3f38357868b341a8b2c4a5ef5bcaffa3
Source dataset
uspto-grants-2009_08
Patent number
US07576094B2

Reaction notes

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