Ethanol → HCID 18354390, compound

HRID 429281Notes

Reaction equation

HRID 429281 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>[OH:24][CH2:23][CH:19]1[O:20][CH2:21][CH2:22][N:17]([C:15]([O:14][C:1]2[C:13]3[CH2:12][C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[C:5]=3[CH:4]=[CH:3][CH:2]=2)=[O:16])[CH2:18]1

Participants

6

Reactant 4

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

Product 1

HCID 18354390HCID 18354390, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3.56 g of methyl 4-fluorenyloxycarbonyl-morpholine-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 of the title compound as a colorless oil. 1H NMR (500 MHz, CDCl3): δ7.77 (d, J=7.6 Hz, 2H), 7.56 (d, J=7.3 Hz, 2H), 7.40 (t, J=7.6 Hz, 2H), 7.32 (t, J=7.3 Hz, 2H), 4.49 (br s, 2H), 4.24 (t, J=6.4 Hz, 1H), 3.24-4.03 (m, 7H), 2.97 (br s, 1H), 2.80 (br t, J=11.7 Hz, 1H).

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-688c8f2cbe59463793082850f4b6e557
Source dataset
uspto-grants-2001_11
Patent number
US06316444B1

Reaction notes

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