Sodium Sulfate → HCID 68566704, compound

HRID 970370Notes

Reaction equation

HRID 970370 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([NH2:14])[C@H:10]([C:15]([F:18])([F:17])[F:16])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[O-]S([O-])(=O)=O.[Na+].[Na+].[O:26]=[C:27]1[NH:32][C:31]2[CH:33]=[C:34]([CH:37]=O)[CH:35]=[CH:36][C:30]=2[S:29][CH2:28]1.[BH4-].[Na+]>C(#N)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([NH:14][CH2:37][C:34]2[CH:35]=[CH:36][C:30]3[S:29][CH2:28][C:27](=[O:26])[NH:32][C:31]=3[CH:33]=2)[C@H:10]([C:15]([F:18])([F:16])[F:17])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 24436Sodium SulfateHCID 4311764Sodium borohydrideHCID 109433483-Oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carbaldehydeHCID 58699962HCID 58699962, compound

Product 1

HCID 68566704HCID 68566704, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (3R,4S)-4-amino-3-(trifluoromethyl)piperidine-1-carboxylic acid tert-butyl ester (2d) (1 equiv.) in acetonitrile is added Na2SO4 and 3-oxo-3,4-dihydro-2H-benzo[1,4]thiazine-6-carboxaldehyde (in) (1 equiv.). After 12 hr at RT, the reaction is filtered through a sintered-glass funnel and the filtrate is concentrated under vacuum. The remaining residue is dissolved in EtOH and NaBH4 (1 equiv.) is added. After 12 h, the reaction is concentrated and the residue is dissolved in 1 N HCl. The solution is neutralized with 6 N NaOH and extracted with EtOAc. The organic fraction is dried over Na2SO4 and concentrated under vacuum. The crude product is purified by flash chromatography on silica gel to afford the title compound.

Workup

  1. filtrationthe reaction is filtered through a sintered-glass funnel
  2. concentrationthe filtrate is concentrated under vacuum
  3. dissolutionThe remaining residue is dissolved in EtOH
  4. waitAfter 12 h
  5. concentrationthe reaction is concentrated
  6. dissolutionthe residue is dissolved in 1 N HCl
  7. extractionextracted with EtOAc
  8. dry with materialThe organic fraction is dried over Na2SO4
  9. concentrationconcentrated under vacuum
  10. customThe crude product is purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-5122e403087a42e2a31cef5d09a8d01a
Source dataset
uspto-grants-2007_12
Patent number
US07312212B2

Reaction notes

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