Sodium borohydride → HCID 86592231, compound

HRID 1355656Notes

Reaction equation

HRID 1355656 reaction equation
[CH:1]([O:4][C:5]([N:7]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([F:20])([F:19])[F:18])=[CH:14][CH:15]=2)[C@H:10]([N:21]([CH2:26][C:27]2[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]=2)[C:22]([O:24][CH3:25])=[O:23])[CH2:9][C@@H:8]1[CH:41]1[CH2:43][CH:42]1[C:44](OCC)=[O:45])=[O:6])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[CH:1]([O:4][C:5]([N:7]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([F:20])([F:19])[F:18])=[CH:14][CH:15]=2)[C@H:10]([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:36])([F:34])[F:35])[CH:32]=2)[C:22]([O:24][CH3:25])=[O:23])[CH2:9][C@@H:8]1[CH:41]1[CH2:43][CH:42]1[CH2:44][OH:45])=[O:6])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86592232HCID 86592232, compound

Product 1

HCID 86592231HCID 86592231, compoundYield 59.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of cis-4-[(3,5-bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-2-(2-ethoxycarbonyl-cyclopropyl)-6-trifluoromethyl-3,4-dihydro-2H-quinoline-1-carboxylic acid isopropyl ester (Example 53) (100 mg, 0.14 mmol) in refluxing methanol (40 ml) was added sodium borohydride (1.0 g) in portions, and the resulting mixture was heated to reflux for an additional 30 min. The cooled reaction was concentrated and the residue was partitioned between ethyl acetate and 2N HCl. The aqueous layer was extracted again with ethyl acetate and the combined extracts were dried (MgSO4), filtered and concentrated. The residue was chromatographed with 15-20% ethyl acetate/hexane to afford the title product (55 mg). MS m/z 657.2 (M+); 1H NMR (CDCl3) δ 3.8 (s, 3H), 3.9 (q, 1H), 7.1 (s, 1H), 7.5 (s, 2H), 7.7 (s, 1H).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for an additional 30 min
  3. customThe cooled reaction
  4. concentrationwas concentrated
  5. customthe residue was partitioned between ethyl acetate and 2N HCl
  6. extractionThe aqueous layer was extracted again with ethyl acetate
  7. dry with materialthe combined extracts were dried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe residue was chromatographed with 15-20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-563ee11c65dd4ed692830ec11782f9db
Source dataset
uspto-grants-2003_07
Patent number
US06586448B1

Reaction notes

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