Ammonium Chloride → tert-Butyl 4-{4-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]-2-(hydroxymethyl)butyl}benzoate

HRID 1920591Notes

Reaction equation

[C:1]([O:5][C:6]([C:8]1[CH:29]=[CH:28][C:11]([CH2:12][CH:13]([CH2:17][CH2:18][C:19]2([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:21][CH2:20]2)[C:14](O)=[O:15])=[CH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl-].[NH4+]>C1COCC1>[CH2:26]([O:25][C:23](=[O:24])[CH2:22][C:19]1([CH2:18][CH2:17][CH:13]([CH2:14][OH:15])[CH2:12][C:11]2[CH:10]=[CH:9][C:8]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])=[CH:29][CH:28]=2)[CH2:21][CH2:20]1)[CH3:27]

Participants

Conditions

Temperature: 0 °C

Procedure

At −10° C., 25.71 ml (25.71 mmol) of a 1 M borane/THF complex solution are added dropwise to a solution of 5199 mg (12.85 mmol) of 2-[4-(tert-butoxycarbonyl)benzyl]-4-[1-(2-ethoxy-2-oxo-ethyl)cyclopropyl]butanoic acid in 100 ml of THF. After warming to 0° C., the mixture is stirred at this temperature for another two hours and then at room temperature for another hour. After complete conversion, saturated ammonium chloride solution is added, and the reaction mixture is extracted three times with in each case 50 ml of ethyl acetate. The combined organic phases are then dried over sodium sulfate, and the solvent is removed to dryness. The crude product obtained is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 2:1). This gives 3412 mg (68% of theory) of a colorless oil.

Workup

waitat room temperature for another hour
extractionthe reaction mixture is extracted three times with in each case 50 ml of ethyl acetate
dry with materialThe combined organic phases are then dried over sodium sulfate
customthe solvent is removed to dryness

Sources & evidence

ORD record: ord-d012ddcdf03c48bb9cf5bca905bcc75b
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08168821B2

Reaction notes

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