Ethyl Acetate → tert-Butyl 4-{[(4-{[1-(hydroxymethyl)cyclopentyl]methoxy}-1,2-benzisoxazol-3-yl)oxy]methyl}-piperidine-1-carboxylate

HRID 2410387Notes

Reaction equation

HRID 2410387 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C:11]1([CH2:16][O:17][C:18]2[C:23]3[C:24]([O:27][CH2:28][CH:29]4[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31][CH2:30]4)=[N:25][O:26][C:22]=3[CH:21]=[CH:20][CH:19]=2)[CH2:15][CH2:14][CH2:13][CH2:12]1)=O.C(OCC)(=O)C>C(OCC)C>[OH:8][CH2:9][C:11]1([CH2:16][O:17][C:18]2[C:23]3[C:24]([O:27][CH2:28][CH:29]4[CH2:34][CH2:33][N:32]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:31][CH2:30]4)=[N:25][O:26][C:22]=3[CH:21]=[CH:20][CH:19]=2)[CH2:15][CH2:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 69320362HCID 69320362, compound

Product 1

HCID 86622737tert-Butyl 4-{[(4-{[1-(hydroxymethyl)cyclopentyl]methoxy}-1,2-benzisoxazol-3-yl)oxy]methyl}-piperidine-1-carboxylateYield 81%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a suspension of lithium aluminum hydride (50.7 mg, 1.34 mmol) in diethyl ether (5 mL) was added an ethereal solution (3 mL) of tert-butyl 4-{[(4-{[1-(methoxycarbonyl)cyclopentyl]methoxy}-1,2-benzisoxazol-3-yl)oxy]methyl}piperidine-1-carboxylate (EXAMPLE 51, step 2, 600 mg, 1.23 mmol) at 0° C. After being stirred for 30 min, ethyl acetate was added to the mixture. Then the mixture was washed with 2N hydrochloric acid and brine. The organic layer was dried over magnesium sulfate and concentrated in vacuo to afford 456 mg (81%) of the title compound as a white solid. The crude product was used in the next step without further purification.

Workup

  1. washThen the mixture was washed with 2N hydrochloric acid and brine
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bdce677457394fc4803ebd38d0767b58
Source dataset
uspto-grants-2014_08
Patent number
US08816090B2

Reaction notes

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