Aluminium lithium hydride → HCID 18723469, compound

HRID 2296820Notes

Reaction equation

HRID 2296820 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][N:11]([C:14]([CH:16]3[CH:20]([C:21]([O:23]CC)=O)[CH2:19][NH:18][CH2:17]3)=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1.CCOCC>[CH2:8]([N:18]1[CH2:19][CH:20]([CH2:21][OH:23])[CH:16]([CH2:14][N:11]2[CH2:12][CH2:13][CH:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)[CH2:9][CH2:10]2)[CH2:17]1)[C:5]1[CH:6]=[CH:7][CH:2]=[CH:3][CH:4]=1

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 131723664HCID 131723664, compound

Product 1

HCID 18723469HCID 18723469, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 6.4 g (14.6 mmol) of 1-benzyl)-3-(RS)-(4-(4-fluorophenyl)piperidinylcarbonyl)-4-(RS)-(ethoxycarbonyl)pyrrolidine in 60 mL of THF at 0° C. was added 17.5 mL (17.5 mmol) of a 1M solution of lithium aluminum hydride (LAH) in ether and the reaction was stirred at 0° C. for 30 min. The reaction mixture was quenched with 5N NaOH. The reaction mixture was extracted with ether and the combined organic fractions were washed with 5N NaOH solution. The organic fractions were dried over Na2SO4, filtered and the filtrate was purified by chromatography [silica, hexanes: ethyl acetate: (2N NH3 in MeOH), 10: 10: 1] to give 4.7 g of the title compound. Spectrum (ESI) m/e=383 (M+1).

Workup

  1. customThe reaction mixture was quenched with 5N NaOH
  2. extractionThe reaction mixture was extracted with ether
  3. washthe combined organic fractions were washed with 5N NaOH solution
  4. dry with materialThe organic fractions were dried over Na2SO4
  5. filtrationfiltered
  6. customthe filtrate was purified by chromatography [silica, hexanes: ethyl acetate: (2N NH3 in MeOH), 10: 10: 1]

Sources & evidence

ORD record
ord-1e0912d658e746ea82bed29c1ecdc7c1
Source dataset
uspto-grants-2002_12
Patent number
US06489354B1

Reaction notes

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