Ammonium Chloride → HCID 67387386, compound

HRID 1444841Notes

Reaction equation

HRID 1444841 reaction equation
[CH2:1]([O:8][C@H:9]([CH3:19])[C:10]([N-]N1CCOCC1)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:20]([Li])([CH3:22])[CH3:21].[Cl-].[NH4+]>C1COCC1.CCCCC>[CH2:1]([O:8][C@@H:9]([C:10](=[O:11])[CH:20]([CH3:22])[CH3:21])[CH3:19])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 178462266HCID 178462266, compoundHCID 178506895HCID 178506895, compound

Product 1

HCID 67387386HCID 67387386, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 8003PentaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (R)-2-benzyloxypropionyl N-morpholinyl amide (10 mmol) in THF (20 mL) under nitrogen atmosphere at −78° C. was added dropwise isopropyl lithium (15 mmol) in pentane. The reaction mixture was stirred at −78 C for 3 h (monitored by tlc). The reaction mixture was poured into saturated ammonium chloride solution and then extracted with ethyl acetate (3×25 mL). The combined extract was washed with water (2×25 mL), dried over Na2SO4 and concentrated in vacuo. The residue was purified by passing through a short silica gel column using a 0-25% gradient of ether and n-pentane as eluents to give pure 20a as a colorless liquid in 94% yield. 1H NMR (400 MHz, CDCl3): δ 1.08 (3H, d); 1.10 (3H, d); 1.36 (3H, d); 3.02 (1H, m); 4.06 (1H, q); 4.46 (2H, dd); 7.33-7.34 (5H, m). MS (ESI) m/z 207.13 (M+H+).

Workup

  1. extractionextracted with ethyl acetate (3×25 mL)
  2. extractionThe combined extract
  3. washwas washed with water (2×25 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified

Sources & evidence

ORD record
ord-801037311d9b4c7c9b96cb3f30667cc4
Source dataset
uspto-grants-2010_02
Patent number
US07662987B2

Reaction notes

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