Methanol → HCID 46785855, compound

HRID 1848894Notes

Reaction equation

HRID 1848894 reaction equation
[N:1]1([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.[O:14]1[CH2:19][CH2:18][C:17](=O)[CH2:16][CH2:15]1.CO.[BH4-].[Na+]>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[O:14]1[CH2:19][CH2:18][CH:17]([N:4]2[CH2:5][CH2:6][N:1]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:2][CH2:3]2)[CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 887MethanolHCID 121599Tetrahydro-4H-pyran-4-oneHCID 143452tert-Butyl piperazine-1-carboxylateHCID 4311764Sodium borohydride

Product 1

HCID 46785855HCID 46785855, compound

Reagents, catalysts & solvents 1

HCID 11026Titanium isopropoxideSolvent

Procedure

To a solution of tert-butyl piperazine-1-carboxylate (5.15 g) and dihydro-2H-pyran-4(3H)-one (3.05 g) stirred for 24 hours at room temperature in titanium(IV) isopropoxide (16.20 mL), methanol (5 mL) was added followed by careful addition of sodium borohydride (2.092 g). The reaction mixture was quenched with water/NaOH solution, extracted with ether, dried over magnesium sulfate, filtered, and concentrated to yield the product. The crude product was used in next step.

Workup

  1. customThe reaction mixture was quenched with water/NaOH solution
  2. extractionextracted with ether
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto yield the product

Sources & evidence

ORD record
ord-a4ac788b659741eabfcd2aeb7839750d
Source dataset
uspto-grants-2015_02
Patent number
US08952157B2

Reaction notes

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