Sodium Chloride → HCID 71073858, compound

HRID 1615399Notes

Reaction equation

HRID 1615399 reaction equation
C([O:3][C:4](=O)[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]2[CH2:18][CH2:17][CH:16]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15][CH2:14]2)=[CH:9][CH:8]=1)C.[H-].C([Al+]CC(C)C)C(C)C.CCCCCC.[Cl-].[Na+].[BH4-].[Na+].[Cl-].[NH4+]>C1(C)C=CC=CC=1.CO>[OH:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([N:13]2[CH2:14][CH2:15][CH:16]([NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:17][CH2:18]2)=[CH:11][CH:12]=1

Participants

8

Reactant 5

HCID 5234Sodium ChlorideHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 21273587HCID 21273587, compoundHCID 71073896HCID 71073896, compound

Product 1

HCID 71073858HCID 71073858, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
-78 °C

Procedure

The 4-(4-tert-butoxycarbonylaminopiperidin-1-yl)-dihydrocinnamic acid ethyl ester (68 g, 0.18 mol) obtained in Example 8(2) was dissolved in toluene (1 L) and cooled to −78° C. A diisobutylaluminum hydride-hexane solution (607 ml, 0.6 mol) was added dropwise. After stirring for 1.5 hours, methanol (10 ml) and a saturated sodium chloride aqueous solution (550 ml) were added, followed by stirring for 3 hours. The insoluble material was filtered with Celite. The solvent was evaporated from the filtrate, and the obtained residue was dissolved in methanol (500 ml) and THF (250 ml). Sodium borohydride (6.9 g, 0.18 mol) was added thereto at 0° C. After stirring for 1 hour, a saturated ammonium chloride aqueous solution was added thereto, followed by extraction with chloroform and drying over magnesium sulfate. After the desiccant was filtered off, the solvent was evaporated, thereby obtaining N-(4-(3-hydroxypropyl)phenyl)-4-tert-butoxycarbonylaminopiperidine (60 g, 98%).

Workup

  1. stirringby stirring for 3 hours
  2. filtrationThe insoluble material was filtered with Celite
  3. customThe solvent was evaporated from the filtrate
  4. dissolutionthe obtained residue was dissolved in methanol (500 ml)
  5. customat 0° C
  6. stirringAfter stirring for 1 hour
  7. extractionfollowed by extraction with chloroform
  8. dry with materialdrying over magnesium sulfate
  9. filtrationAfter the desiccant was filtered off
  10. customthe solvent was evaporated

Sources & evidence

ORD record
ord-a89eaefafdcc488da9d6e3f6a4bc40fb
Source dataset
uspto-grants-2014_07
Patent number
US08765750B2

Reaction notes

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