Ethanol → HCID 18354390, compound

HRID 2300804Notes

Reaction equation

HRID 2300804 reaction equation
[C:1]1([O:14][C:15]([N:17]2[CH2:22][CH2:21][O:20][CH:19]([C:23](OC)=[O:24])[CH2:18]2)=[O:16])[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[Cl-].[Li+].[BH4-].[Na+].C(O)C>C1COCC1>[C:1]1([O:14][C:15]([N:17]2[CH2:22][CH2:21][O:20][CH:19]([CH2:23][OH:24])[CH2:18]2)=[O:16])[C:13]2[CH2:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 69961590HCID 69961590, compound

Product 1

HCID 18354390HCID 18354390, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3.56 g of methyl 4-fluorenyloxycarbonylmorpholine-2-carboxylate in 25 mL of THF was added 0.58 g of lithium chloride, 0.52 g of sodium borohydride, and 25 mL of ethanol. The mixture was stirred overnight at room temperature, concentrated, and redissolved in 200 mL of CH2Cl2. This CH2Cl2 solution was washed with 2×100 mL of water and 100 mL of brine, dried over MgSO4, and concentrated. The residue was purified by flash chromatography, eluting with 1:1 hexanes-EtOAc, to yield 2.34 g of the title compound as a colorless oil.

Workup

  1. concentrationconcentrated
  2. dissolutionredissolved in 200 mL of CH2Cl2
  3. washThis CH2Cl2 solution was washed with 2×100 mL of water and 100 mL of brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography
  7. washeluting with 1:1 hexanes-EtOAc

Sources & evidence

ORD record
ord-8b0c5e07f6d240faa95d395ce14180f9
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

Loading…