Aluminium lithium hydride → HCID 22315173, compound

HRID 430188Notes

Reaction equation

HRID 430188 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:29])[CH:12]([C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[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:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=2)[C:11]([NH:10][C:7]2[CH:8]=[CH:9][C:4]([CH2:3][OH:2])=[CH:5][N:6]=2)=[O:29])[CH2:15][CH2:16][CH2:17][CH2:18]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 54426411HCID 54426411, compound

Product 1

HCID 22315173HCID 22315173, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 6-[3-cyclopentyl-2-(4-methanesulfonyl-phenyl)-propionylamino]-nicotinic acid methyl ester (prepared in example 53(B)(a), 110 mg, 0.26 mmol) in diethyl ether (500 μL) was cooled to 0° C. and then slowly treated with lithium aluminum hydride (15 mg, 0.38 mmol). The reaction mixture was stirred at 0° C. for 30 min then allowed to warm to 25° C. After 1 h at 25° C., thin layer chromatography still indicated the presence of the starting material. An additional amount of lithium aluminum hydride (10 mg, 0.26 mmol) was added to the reaction mixture, and the reaction mixture was allowed to stir at 25° C. for 1 h. The reaction mixture was then slowly quenched by the dropwise addition of water (10 mL). The resulting mixture was partitioned between water and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, ⅓ hexanes/ethyl acetate) afforded the 3-cyclopentyl-N-(5-hydroxymethyl-pyridin-2-yl)-2-(4-methanesulfonyl-phenyl)-propionamide (60 mg, 57%) as a yellow foam: mp 74-77° C.; EI-HRMS m/e calcd for C21H26N2O4S (M+) 402.1613, found 402.1617.

Workup

  1. customwas cooled to 0° C.
  2. temperatureto warm to 25° C
  3. waitAfter 1 h at 25° C.
  4. stirringto stir at 25° C. for 1 h
  5. customThe reaction mixture was then slowly quenched by the dropwise addition of water (10 mL)
  6. customThe resulting mixture was partitioned between water and ethyl acetate
  7. dry with materialThe organic layer was dried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6cc0ded3fb7549b48fab1ba7328c9eb6
Source dataset
uspto-grants-2001_11
Patent number
US06320050B1

Reaction notes

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