Sodium Bicarbonate → HCID 22137413, compound

HRID 1827554Notes

Reaction equation

HRID 1827554 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]=[CH:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][O:25]3)[CH:18]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].C(=O)(O)[O-].[Na+]>CO.C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([O:23][CH:24]3[CH2:29][CH2:28][CH2:27][CH2:26][O:25]3)[CH:18]=2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 22137366HCID 22137366, compound

Product 1

HCID 22137413HCID 22137413, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (4-benzyloxy-phenyl)-[3-(tetrahydro-pyran-2-yloxy)-benzylidene]-amine (21.0 g, 54.2 mmol) in 350 mL methanol and 150 mL methylene chloride at 0° C. was added sodium borohydride (3.3 g, 86.7 mmol) in portions over 20 minutes. The reaction mixture was stirred at 0° C. for 1 hr. and at room temperature for 3 days. Saturated aqueous sodium bicarbonate (250 mL) was added and the aqueous solution was washed with methylene chloride (3×500 mL). The combined organic layers were washed with 500 mL saturated aqueous sodium chloride, dried (magnesium sulfate), filtered, and concentrated to afford 20.6 of the title compound of Step B.

Workup

  1. waitand at room temperature for 3 days
  2. washthe aqueous solution was washed with methylene chloride (3×500 mL)
  3. washThe combined organic layers were washed with 500 mL saturated aqueous sodium chloride
  4. dry with materialdried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b2e39487e51948839f159edae07a3a9f
Source dataset
uspto-grants-2006_05
Patent number
US07053212B2

Reaction notes

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