Tetrahydro-4H-pyran-4-one → HCID 58117128, compound

HRID 2066552Notes

Reaction equation

HRID 2066552 reaction equation
[C:1]([O:5][C:6](=[O:11])[NH:7][CH2:8][CH2:9][NH2:10])([CH3:4])([CH3:3])[CH3:2].[O:12]1[CH2:17][CH2:16][C:15](=O)[CH2:14][CH2:13]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.[NH4+].[OH-].O>[C:1]([O:5][C:6](=[O:11])[NH:7][CH2:8][CH2:9][NH:10][CH:15]1[CH2:16][CH2:17][O:12][CH2:13][CH2:14]1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 3

HCID 121599Tetrahydro-4H-pyran-4-oneHCID 187201N-BOC-ethylenediamineHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 58117128HCID 58117128, compoundYield 99.7%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 14923Ammonium HydroxideSolvent

Procedure

To a solution of (2-amino-ethyl)-carbamic acid tert-butyl ester (5 g, 31.2 mmol) in DCE (150 mL) was added tetrahydro-pyran-4-one (2.7 mg, 27.1 mmol). The mixture was stirred at RT for 1 h, then sodium triacetoxyborohydride (8.63 g, 40.7 mmol) was added and stirring was continued for 18 h. The reaction mixture was diluted with NH4OH 10% in water and extracted with DCM. The organic layer was separated, dried (Na2SO4) and concentrated in vacuo to give the title compound as colourless oil (6.60 g, 99%).

Workup

  1. stirringstirring
  2. waitwas continued for 18 h
  3. extractionextracted with DCM
  4. customThe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fa8ad712eda9492b8fb782cb86cd28b0
Source dataset
uspto-grants-2012_10
Patent number
US08293735B2

Reaction notes

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