Sodium Sulfate → HCID 86635360, compound

HRID 657121Notes

Reaction equation

HRID 657121 reaction equation
[F:1][C:2]([F:23])([F:22])[S:3]([O:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([F:17])=[CH:14][CH:15]=2)[N:10]([CH2:18][CH:19]=O)[C:9](=[O:21])[CH:8]=1)(=[O:5])=[O:4].[O:24]1[C:33]2[CH:32]=[C:31]([CH2:34][N:35]([CH:43]3[CH2:48][CH2:47][NH:46][CH2:45][CH2:44]3)[C:36](=[O:42])[O:37][C:38]([CH3:41])([CH3:40])[CH3:39])[N:30]=[CH:29][C:28]=2[O:27][CH2:26][CH2:25]1.S([O-])([O-])(=O)=O.[Na+].[Na+].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1.C(OCC)(=O)C>[F:23][C:2]([F:1])([F:22])[S:3]([O:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([F:17])=[CH:14][CH:15]=2)[N:10]([CH2:18][CH2:19][N:46]2[CH2:47][CH2:48][CH:43]([N:35]([CH2:34][C:31]3[N:30]=[CH:29][C:28]4[O:27][CH2:26][CH2:25][O:24][C:33]=4[CH:32]=3)[C:36]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:42])[CH2:44][CH2:45]2)[C:9](=[O:21])[CH:8]=1)(=[O:5])=[O:4]

Participants

7

Reactant 4

HCID 24436Sodium SulfateHCID 5049666Sodium triacetoxyborohydrideHCID 578154611,1-Dimethylethyl (2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)-4-piperidinylcarbamateHCID 86635361HCID 86635361, compound

Product 1

HCID 86635360HCID 86635360, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

The crude 7-fluoro-2-oxo-1-(2-oxoethyl)-1,2-dihydro-4-quinolinyl trifluoromethanesulfonate (5.6 g, 15.9 mmol assumed 100% from previous step) was dissolved in THF (50 ml) and 1,1-dimethylethyl (2,3-dihydro[1,4]dioxino[2,3-c]pyridin-7-ylmethyl)-4-piperidinylcarbamate (for a synthesis see WO2004/058144 Example 99(h)) (5.60 g, 15.9 mmol) added followed by sodium sulphate (˜15 g). After 2 h sodium triacetoxyborohydride (12.3 g, 58 mmol) was added portionwise over 1 h and the solution stirred for 18 h. The solution was diluted with ethyl acetate and washed with sodium bicarbonate solution, dried and concentrated. Chromatography (70 g silica SPE, eluting with ethyl acetate) provided product (4.88 g) contaminated with an impurity. Further chromatography (70 g silica SPE gradient elution with 2:1 ethyl acetate/hexane to ethyl acetate to ethyl acetate/10% methanol) provided the title compound as a clear oil (2.81 g, 26%).

Workup

  1. additionadded
  2. washwashed with sodium bicarbonate solution
  3. customdried
  4. concentrationconcentrated
  5. washChromatography (70 g silica SPE, eluting with ethyl acetate)

Sources & evidence

ORD record
ord-6ec867cac1e84d08bff7d47c4c4f99da
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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