Water → Ammonium Hydroxide

HRID 1858108Notes

Reaction equation

HRID 1858108 reaction equation
C([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:30])=[C:24]([CH2:27]C=C)[CH:25]=2)[NH:20][C:19](=[O:31])[C:18]=1[C:32]1[CH:37]=[C:36]([CH3:38])[CH:35]=[C:34]([CH3:39])[CH:33]=1)=[O:7])(C)(C)C.[O:40]1[CH2:44][CH2:43]CC1.O.C[N+]1([O-])CC[O:50]CC1.[C:54]([OH:58])([CH3:57])([CH3:56])[CH3:55]>[Os](=O)(=O)(=O)=O>[OH-:5].[NH4+:8].[C:54]([O:58][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][C:23]([Cl:30])=[C:24]([CH2:27][CH:44]([OH:40])[CH2:43][OH:50])[CH:25]=2)[NH:20][C:19](=[O:31])[C:18]=1[C:32]1[CH:33]=[C:34]([CH3:39])[CH:35]=[C:36]([CH3:38])[CH:37]=1)=[O:7])([CH3:57])([CH3:56])[CH3:55]

Participants

8

Reactant 5

HCID 962WaterHCID 6386tert-ButanolHCID 8028TetrahydrofuranHCID 82029Methyl morpholine oxideHCID 538248342-{2-[6-Allyl-7-chloro-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

Product 2

HCID 14923Ammonium HydroxideYield 10%HCID 540195562-{2-[7-Chloro-6-(2,3-dihydroxypropyl)-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

To a solution of 2-{2-[6-allyl-7-chloro-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester (EXAMPLE 4.1 Step E, 6.0 g in a mixture of 80 mL tert-butanol, 24 mL tetrahydrofuran and 8 mL water) was added 1.4 g 4-methylmorpholine N-oxide followed by 140 mg osmium tetraoxide and the mixture stirred at room temperature. After 20 hours, the mixture was concentrated in vacuo and the residue dissolved in ethyl acetate and washed sequentially with water and brine. The combined organics were dried over sodium sulfate and purified by flash chromatography on silica gel (ethyl acetate:hexane, 1:1; then methylene chloride:10% ammonium hydroxide in methanol, 9:1) to give the title compound (5.7 g).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. dissolutionthe residue dissolved in ethyl acetate
  3. washwashed sequentially with water and brine
  4. dry with materialThe combined organics were dried over sodium sulfate
  5. custompurified by flash chromatography on silica gel (ethyl acetate

Sources & evidence

ORD record
ord-b9c281a315e94c9d910aa18f430d9851
Source dataset
uspto-grants-2000_11
Patent number
US06150352

Reaction notes

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