Methanol → HCID 117643490, compound

HRID 2171270Notes

Reaction equation

HRID 2171270 reaction equation
CO.[BH4-].[Na+].[CH2:5]([N:12]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C@H:13]([C:15](=[O:20])[CH:16]=[C:17]([CH3:19])[CH3:18])[CH3:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Cl-].[Ce+3].[Cl-].[Cl-]>O>[CH2:5]([N:12]([CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C@H:13]([CH:15]([OH:20])[CH:16]=[C:17]([CH3:18])[CH3:19])[CH3:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 887Methanol2×HCID 24636Cerium(III) chlorideHCID 4311764Sodium borohydrideHCID 89666932HCID 89666932, compound

Product 1

HCID 117643490HCID 117643490, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A methanol solution (10 ml) containing sodium borohydride (1.5 g) and (S)-2-(dibenzylamino)-5-methyl-4-hexen-3-one (4.2 g) obtained in the 3rd step were added to an MeOH (30 ml) solution containing cerium chloride (10 g), followed by stirring for 7 hours. Water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layers were washed with water and saturated saline and dried over anhydrous sodium sulfate. Then, the solvent was distilled away under reduced pressure and the obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0 to 1:0.2). A yellow liquid of (2S)-2-(dibenzylamino)-5-methyl-4-hexen-3-ol (3.5 g) was thus obtained.

Workup

  1. customobtained in the 3rd step
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic layers were washed with water and saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThen, the solvent was distilled away under reduced pressure
  6. customthe obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=1:0 to 1:0.2)

Sources & evidence

ORD record
ord-0e45146a057144eb8c975fdf613c7f29
Source dataset
uspto-grants-2015_06
Patent number
US09051310B2

Reaction notes

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