Aluminium lithium hydride → HCID 10182411, compound

HRID 1935251Notes

Reaction equation

HRID 1935251 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:35])[CH:12]([C:19]2[CH:24]=[CH:23][C:22]([C:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:28]=[CH:27][CH:26]=3)=[CH:21][CH:20]=2)[CH2:13][CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[N:6][CH:5]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[CH:14]1([CH2:13][CH:12]([C:19]2[CH:20]=[CH:21][C:22]([C:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:28]=[CH:27][CH:26]=3)=[CH:23][CH:24]=2)[C:11]([NH:10][C:7]2[CH:8]=[CH:9][C:4]([CH2:3][OH:2])=[CH:5][N:6]=2)=[O:35])[CH2:15][CH2:16][CH2:17][CH2:18]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 67483603HCID 67483603, compound

Product 1

HCID 10182411HCID 10182411, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A solution 6-[3-cyclopentyl-2-(4-naphthalen-1-yl-phenyl)-propionylamino]-nicotinic acid methyl ester (prepared in Example 25B-a, 140 mg, 0.29 mmol) in diethyl ether (2 mL) was cooled to 0° C. and then slowly treated with lithium aluminum hydride powder (17 mg, 0.44 mmol). The reaction mixture was stirred at 0° C. for 30 min and then allowed to warm to 25° C. where it was stirred for 3.5 h. The reaction mixture was then slowly quenched by the dropwise addition of water (5 mL). The resulting mixture was partitioned between water (25 mL) and ethyl acetate (25 mL), and the layers were separated. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 1/1 hexanes/ethyl acetate) afforded 3-cyclopentyl-N-(5-hydroxymethyl-pyridin-2-yl)-2-(4-naphthalen-1-yl-phenyl)-propionamide (47 mg, 37%) as a light yellow foam: mp 72-75° C.; EI-HRMS m/e calcd for C30H30N2O2 (M+) 450.2307, found 450.2312.

Workup

  1. temperatureto warm to 25° C. where it
  2. stirringwas stirred for 3.5 h
  3. customThe reaction mixture was then slowly quenched by the dropwise addition of water (5 mL)
  4. customThe resulting mixture was partitioned between water (25 mL) and ethyl acetate (25 mL)
  5. customthe layers were separated
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-62ad74329bfd409da64ccb6d9527f225
Source dataset
uspto-grants-2002_05
Patent number
US06384220B2

Reaction notes

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