Acetone → (2-(2-Amino-3-morpholinoquinolin-6-yl)-3-methylphenyl)(phenyl)methanol

HRID 1028965Notes

Reaction equation

HRID 1028965 reaction equation
[NH2:1][C:2]1[C:11]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:18]3[C:23]([CH3:24])=[CH:22][CH:21]=[CH:20][C:19]=3[C:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[O:26])[CH:8]=2)[N:3]=1.[BH4-].[Na+].CC(C)=O>CO>[NH2:1][C:2]1[C:11]([N:12]2[CH2:13][CH2:14][O:15][CH2:16][CH2:17]2)=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:18]3[C:23]([CH3:24])=[CH:22][CH:21]=[CH:20][C:19]=3[CH:25]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[OH:26])[CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 180AcetoneHCID 4311764Sodium borohydride2×HCID 67325753(2-(2-Amino-3-morpholinoquinolin-6-yl)-3-methylphenyl)(phenyl)methanone

Product 1

HCID 67350995(2-(2-Amino-3-morpholinoquinolin-6-yl)-3-methylphenyl)(phenyl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a cooled (ice bath) solution of (2-(2-amino-3-morpholinoquinolin-6-yl)-3-methylphenyl)(phenyl)methanone (0.246 g, 0.581 mmol, prepared as in Example 15, Step 1) in MeOH (10.0 mL) was added sodium tetrahydroborate (0.044 g, 1.162 mmol) in one portion. The reaction mixture was then allowed to warm to RT and stirred for 17 h (overnight). Additional 4 eq of NaBH4 was added and stirred for 7 h until the conversion was completed, determined by LCMS. Acetone was added to quench the excess NaBH4. The resulted solution was concentrated and dried in vacuum to afford crude (2-(2-amino-3-morpholinoquinolin-6-yl)-3-methylphenyl) (phenyl)methanol as light yellow solid which was used without further purification.

Workup

  1. stirringstirred for 7 h until the conversion
  2. customto quench the excess NaBH4
  3. concentrationThe resulted solution was concentrated
  4. customdried in vacuum

Sources & evidence

ORD record
ord-3b6ed755f8a544079d8d3d3aba8982a5
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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