Water → (3,5-Bis-trifluoromethyl-benzyl)-(7,8-dimethoxy-1-oxo-3,3a,4,5-tetrahydro-2-oxa-9b-aza-cyclopenta[a]naphthalen-5-yl)-carbamic Acid Methyl Ester

HRID 1530902Notes

Reaction equation

HRID 1530902 reaction equation
C([O:3][C:4]([C@H:6]1[CH2:15][C@@H:14]([N:16]([CH2:21][C:22]2[CH:27]=[C:26]([C:28]([F:31])([F:30])[F:29])[CH:25]=[C:24]([C:32]([F:35])([F:34])[F:33])[CH:23]=2)[C:17]([O:19][CH3:20])=[O:18])[C:13]2[C:8](=[CH:9][C:10]([O:38][CH3:39])=[C:11]([O:36][CH3:37])[CH:12]=2)[N:7]1[C:40](OC(CC)C)=[O:41])=O)C.[BH4-].[Na+].O>CO>[CH3:20][O:19][C:17](=[O:18])[N:16]([CH2:21][C:22]1[CH:23]=[C:24]([C:32]([F:35])([F:34])[F:33])[CH:25]=[C:26]([C:28]([F:29])([F:30])[F:31])[CH:27]=1)[CH:14]1[C:13]2[C:8](=[CH:9][C:10]([O:38][CH3:39])=[C:11]([O:36][CH3:37])[CH:12]=2)[N:7]2[C:40](=[O:41])[O:3][CH2:4][CH:6]2[CH2:15]1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 86592230cis-4-[(3,5-Bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-6,7-dimethoxy-3,4 dihydro-2H-quinoline-1,2-dicarboxylic acid 2-butyl ester 1-ethyl ester

Product 1

HCID 86756497(3,5-Bis-trifluoromethyl-benzyl)-(7,8-dimethoxy-1-oxo-3,3a,4,5-tetrahydro-2-oxa-9b-aza-cyclopenta[a]naphthalen-5-yl)-carbamic Acid Methyl EsterYield 85.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of cis 4-[(3,5-bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-6,7-dimethoxy-3,4-dihydro-2H-quinoline-1,2-dicarboxylic acid 2-butyl ester 1-ethyl ester (Example 5) (100 mg, 0.15 mmol) in 8.5 mL methanol at 0° C. was added sodium borohydride (57 mg, 1.5 mmol) and the resulting mixture was stirred at room temperature for 1 h. The reaction mixture was poured into water and extracted twice with ethyl acetate. The combined extracts were dried over magnesium sulfate, filtered and concentrated. The residue was chromatographed using 80% ethyl acetate/hexanes to afford the title product (70 mg). 1H NMR (CDCl3) δ 1.8 (br, 1H), 2.4 (br, I H), 3.6 (s, 3H), 6.5 (br, 1H), 7.6 (br, 2H), 7.9 (s, 1H).

Workup

  1. extractionextracted twice with ethyl acetate
  2. dry with materialThe combined extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was chromatographed

Sources & evidence

ORD record
ord-25087b69d13743f88210291000d7ff1c
Source dataset
uspto-grants-2001_03
Patent number
US06197786B1

Reaction notes

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