Methanol → HCID 46785855, compound

HRID 624414Notes

Reaction equation

HRID 624414 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-2f632c99848f417db73bd36f50301e0f
Source dataset
uspto-grants-2016_04
Patent number
US09303025B2

Reaction notes

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