Ammonium Chloride → Methyl 4-[5-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]-3-(hydroxymethyl)pentyl]benzoate

HRID 1920577Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:27])[CH2:5][C:6]1([CH2:9][CH2:10][CH:11]([CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:25][CH3:26])=[O:24])=[CH:19][CH:18]=2)[C:12](O)=[O:13])[CH2:8][CH2:7]1)[CH3:2].[Cl-].[NH4+]>C1COCC1>[CH2:1]([O:3][C:4](=[O:27])[CH2:5][C:6]1([CH2:9][CH2:10][CH:11]([CH2:12][OH:13])[CH2:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([O:25][CH3:26])=[O:24])=[CH:19][CH:18]=2)[CH2:8][CH2:7]1)[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

At −10° C., 2.13 ml of a 1 M borane/THF complex solution (2.13 mmol) are added dropwise to a solution of 400 mg (1.06 mmol) of 4-[1-(2-ethoxy-2-oxoethyl)cyclopropyl]-2-{2-[4-(methoxy-carbonyl)phenyl]ethyl}butanoic acid in 10 ml of THF. After warming to 0° C., the mixture is stirred at this temperature for another 2 hours. After complete conversion, saturated ammonium chloride solution is added, and the reaction mixture is extracted three times with 20 ml of ethyl acetate. The combined organic phases are then dried over sodium sulfate, and the solvent is evaporated to dryness. This gives 330 mg (85% of theory) of a colorless oil.

Workup

extractionthe reaction mixture is extracted three times with 20 ml of ethyl acetate
dry with materialThe combined organic phases are then dried over sodium sulfate
customthe solvent is evaporated to dryness

Sources & evidence

ORD record: ord-998a24fdefdf4d98999051816ccc52d0
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08168821B2

Reaction notes

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