Methanol → HCID 86756027, compound

HRID 1937467Notes

Reaction equation

HRID 1937467 reaction equation
C[O:2][C:3]([C:5]1[CH:14]=[C:13]2[C:8]([C@H:9]([N:21]([CH2:26][C:27]3[CH:32]=[C:31]([C:33]([F:36])([F:35])[F:34])[CH:30]=[C:29]([C:37]([F:40])([F:39])[F:38])[CH:28]=3)[C:22]([O:24][CH3:25])=[O:23])[CH2:10][C@H:11]([CH3:20])[N:12]2[C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:7][C:6]=1[O:41][CH3:42])=O.[BH4-].[Na+].CO>O1CCCC1>[CH2:18]([O:17][C:15]([N:12]1[C:13]2[C:8](=[CH:7][C:6]([O:41][CH3:42])=[C:5]([CH2:3][OH:2])[CH:14]=2)[C@H:9]([N:21]([CH2:26][C:27]2[CH:28]=[C:29]([C:37]([F:38])([F:39])[F:40])[CH:30]=[C:31]([C:33]([F:35])([F:34])[F:36])[CH:32]=2)[C:22]([O:24][CH3:25])=[O:23])[CH2:10][C@@H:11]1[CH3:20])=[O:16])[CH3:19]

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 86756028HCID 86756028, compound

Product 1

HCID 86756027HCID 86756027, compoundYield 108%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of cis-4-[(3,5-bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-6-methoxy-2-methyl-3,4-dihydro-2H-quinoline-1,7-dicarboxylic acid 1-ethyl ester 7-methyl ester (Example 13) (100 mg; 0.16 mmol) in 20 mL tetrahydrofuran was added sodium borohydride (62 mg; 1.6 mmol). The reaction was heated to reflux and methanol (40 mL) was added slowly. After an additional 30 min at reflux the reaction was concentrated and the residue was diluted with 20 ml H2O and extracted 3×50 mL of ethyl acetate. The combined extracts were dried (MgSO4), filtered, concentrated, and the residue was purified by chromatography (30-40% ethyl acetate:hexane) to afford 100 mg of the title product. 1H NMR (CDCl3) δ 1.1 (d, 3H), 1.3 (t, 3H), 3.75 (s, 3H), 6.4 (s, 1H), 7.4 (s, 1H), 7.7 (s, 2H), 7.8 (s, 1H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux
  3. temperatureAfter an additional 30 min at reflux the reaction
  4. concentrationwas concentrated
  5. additionthe residue was diluted with 20 ml H2O
  6. extractionextracted 3×50 mL of ethyl acetate
  7. dry with materialThe combined extracts were dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customthe residue was purified by chromatography (30-40% ethyl acetate:hexane)

Sources & evidence

ORD record
ord-ca1ad674fc5741abbae1164d6f9f729d
Source dataset
uspto-grants-2002_05
Patent number
US06395751B1

Reaction notes

Loading…