Methanol → HCID 53912795, compound

HRID 1757241Notes

Reaction equation

HRID 1757241 reaction equation
[F:1][C:2]([F:35])([F:34])[C:3]1[CH:4]=[C:5]([CH2:13][O:14][C@@H:15]2[CH2:20][CH2:19][CH2:18][N:17]([C:21]([C:23]3[O:24][CH:25]=[CH:26][CH:27]=3)=O)[C@@H:16]2[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.CO>O1CCCC1>[F:12][C:9]([F:10])([F:11])[C:7]1[CH:6]=[C:5]([CH2:13][O:14][C@@H:15]2[CH2:20][CH2:19][CH2:18][N:17]([CH2:21][C:23]3[O:24][CH:25]=[CH:26][CH:27]=3)[C@@H:16]2[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:4]=[C:3]([C:2]([F:35])([F:34])[F:1])[CH:8]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 53748592HCID 53748592, compound

Product 1

HCID 53912795HCID 53912795, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound of Example 9 (340 mg) was dissolved in tetrahydrofuran. To this solution was added borane-dimethyl sulfide complex (0.18 ml of 10M solution) and the resulting solution was heated at reflux for 8 h. The mixture was cooled, methanol added to quench excess borane, and the solvents were removed in vacuo. The residue was dissolved in methanol (10 ml) and potassium carbonate was added (238 mg). This mixture was heated at reflux for 1 hour; the methanol was removed in vacuo and the residue was dispersed between ethyl acetate and brine. The ethyl acetate layer was dried (MgSO4) and evaporated. The residue was purified by chromatography on silica using 10% ethyl acetate in petrol. The product was recrystallised from ether-hexane: mp 103°-104° C. 1H NMR d 1.4-1.5 (2H, m, CH2CH2), 1.8-1.9 (1H, m, CHHCH2N), 2.1-2.2 (2H, m, CHHCH2N and CHHN), 2.95-3.0 (1H, m, CHHN), 3.11-3.15 (1H, d, J=15.0 Hz, NCHH-furan), 3.38 (1H, s, NCHCHO), 3.54-3.58 (1H, d, J=15.0 Hz, NCHH-furan), 3.56 (1H, s, NCHCHO), 4.02-4.06 (1H, d, J=13.0 Hz, OCH H--), 4.59-4.62 (1H, d, J=13.0 Hz, OCHH--), 6.08-6.09 (1H, m, furan H), 6.35-6.36 (1H, m, furan-H), 7.24-7.32 (3H, m, ArH), 7.46-7.48 (2H, m, ArH), 7.55 (1H, s, furan-H), 7.68 (2H, s, ArH), 7.93 (1H, s, ArH); MS (CI+) m/z 485 (M+ +1, 100%). Found: C, 62.11; H, 4.80; N, 2.90. Calcd. for C25H23NF6O: C, 62.27; H, 4.83; N, 2.96.

Workup

  1. additionTo this solution was added borane-dimethyl sulfide complex (0.18 ml of 10M solution)
  2. temperaturethe resulting solution was heated
  3. temperatureat reflux for 8 h
  4. temperatureThe mixture was cooled
  5. customto quench excess borane
  6. customthe solvents were removed in vacuo
  7. dissolutionThe residue was dissolved in methanol (10 ml)
  8. additionpotassium carbonate was added (238 mg)
  9. temperatureThis mixture was heated
  10. temperatureat reflux for 1 hour
  11. customthe methanol was removed in vacuo
  12. additionthe residue was dispersed between ethyl acetate and brine
  13. dry with materialThe ethyl acetate layer was dried (MgSO4)
  14. customevaporated
  15. customThe residue was purified by chromatography on silica using 10% ethyl acetate in petrol
  16. customThe product was recrystallised from ether-hexane

Sources & evidence

ORD record
ord-f60f3be7e65a40ada63a90afd50ed308
Source dataset
uspto-grants-1995_08
Patent number
US05444074

Reaction notes

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