Sodium borohydride → (2-(2-amino-3-morpholinoquinolin-6-yl)phenyl)(tetrahydro-2H-pyran-4-yl)methanol

HRID 1028956Notes

Reaction equation

HRID 1028956 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[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]([CH:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)=[O:25])[CH:8]=2)[N:3]=1.[BH4-].[Na+]>CO>[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[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[CH:24]([CH:26]3[CH2:27][CH2:28][O:29][CH2:30][CH2:31]3)[OH:25])[CH:8]=2)[N:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 53328643(2-(2-amino-3-morpholinoquinolin-6-yl)phenyl)(tetrahydro-2H-pyran-4-yl)methanone

Product 1

HCID 53328818(2-(2-amino-3-morpholinoquinolin-6-yl)phenyl)(tetrahydro-2H-pyran-4-yl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

(2-(2-Amino-3-morpholinoquinolin-6-yl)phenyl)(tetrahydro-2H-pyran-4-yl)methanone (0.164 g, 0.393 mmol, see Example 11) was dissolved in MeOH (20 mL) and treated with sodium borohydride (0.021 mL, 0.589 mmol). After 10 min, the solution was heated to 40° C. for an additional 15 minutes, then evaporated to dryness under reduced pressure. The crude material was partitioned between water (20 mL), saturated sodium bicarbonate (20 mL), and ethyl acetate (40 mL). The organic layer was dried with magnesium sulfate and evaporated to dryness under reduced pressure and the crude material was purified by silica chromatography (10-100% hexane in ethyl acetate gradient. The product peak which eluted was concentrated to give (2-(2-amino-3-morpholinoquinolin-6-yl)phenyl)(tetrahydro-2H-pyran-4-yl)methanol. MS (ESI, pos. ion) m/z: 420 (M+1).

Workup

  1. customevaporated to dryness under reduced pressure
  2. customThe crude material was partitioned between water (20 mL), saturated sodium bicarbonate (20 mL), and ethyl acetate (40 mL)
  3. dry with materialThe organic layer was dried with magnesium sulfate
  4. customevaporated to dryness under reduced pressure
  5. customthe crude material was purified by silica chromatography (10-100% hexane in ethyl acetate gradient
  6. washThe product peak which eluted
  7. concentrationwas concentrated

Sources & evidence

ORD record
ord-3343a55476b84d8eb2700d35ebb8f61a
Source dataset
uspto-grants-2014_05
Patent number
US08735384B2

Reaction notes

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