Lithium → HCID 9895960, compound

HRID 568094Notes

Reaction equation

HRID 568094 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH2:15][CH:16]([N:28]([CH2:40][C:41]2[CH:46]=[CH:45][C:44]([C:47]([CH3:50])([CH3:49])[CH3:48])=[CH:43][CH:42]=2)[CH2:29][C:30]2[CH:35]=[CH:34][C:33]([C:36]([CH3:39])([CH3:38])[CH3:37])=[CH:32][CH:31]=2)[C:17]([NH:19][CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=O)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:15][CH:16]([N:28]([CH2:40][C:41]2[CH:46]=[CH:45][C:44]([C:47]([CH3:50])([CH3:49])[CH3:48])=[CH:43][CH:42]=2)[CH2:29][C:30]2[CH:31]=[CH:32][C:33]([C:36]([CH3:37])([CH3:38])[CH3:39])=[CH:34][CH:35]=2)[CH2:17][NH:19][CH2:20][CH2:21][N:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 3028194LithiumHCID 18352010HCID 18352010, compound

Product 1

HCID 9895960HCID 9895960, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 900 mg (1.75 mmol) 3-(4-benzyloxy-phenyl)-2-[bis-(4-tert-butyl-benzyl)-amino]-N-(2-piperidin-1-yl-ethyl)-propionamide (Example 10) in 36 mL dry THF was treated portionwise with 332 mg (8.76 mmol) lithium tetrahydriodoaluminate, and the resulting suspension was heated under reflux for 16 hours. The mixture was then carefully quenched with 0.4 mL H2O, followed by 2.0 mL 2N NaOH solution, and finally 0.8 mL H2O. The mixture was filtered and the solids washed with chloroform. The filtrate was treated with 50 mL H2O, and after layers separated, the aqueous layer was extracted with an additional 50 mL chloroform. The combined organic extracts were washed with brine, dried over anhydrous magnesium sulphate, and concentrated at reduced pressure to give 832 mg of an amber oil. The oil was purified by column chromatography on silica gel (230-400 mesh) using 2% to 5% methanol in chloroform as eluant to give 612 mg (69%) of the title compound as a viscous, pale yellow liquid.

Workup

  1. temperaturethe resulting suspension was heated
  2. temperatureunder reflux for 16 hours
  3. customThe mixture was then carefully quenched with 0.4 mL H2O
  4. filtrationThe mixture was filtered
  5. washthe solids washed with chloroform
  6. additionThe filtrate was treated with 50 mL H2O
  7. customafter layers separated
  8. extractionthe aqueous layer was extracted with an additional 50 mL chloroform
  9. washThe combined organic extracts were washed with brine
  10. dry with materialdried over anhydrous magnesium sulphate
  11. concentrationconcentrated at reduced pressure

Sources & evidence

ORD record
ord-aaf9a11c57944df7919d3283a305471a
Source dataset
uspto-grants-2001_01
Patent number
US06180677B2

Reaction notes

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