Hydrochloric Acid → HCID 21949695, compound

HRID 2215179Notes

Reaction equation

[C:1]([CH2:3][C:4]1[CH:20]=[CH:19][C:7]([O:8][C:9]([CH3:18])([CH3:17])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:6][CH:5]=1)#[N:2].Cl.C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1>[NH2:2][CH2:1][CH2:3][C:4]1[CH:5]=[CH:6][C:7]([O:8][C:9]([CH3:18])([CH3:17])[C:10]([O:12][C:13]([CH3:14])([CH3:16])[CH3:15])=[O:11])=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 50 °C

Procedure

tert-Butyl 2-[4-(cyanomethyl)phenoxy]-2-methylpropionate (5.50 g, 20.0 mmol) was dissolved in tetrahydrofuran (90 mL). Subsequently, in a nitrogen atmosphere, borane-tetrahydrofuran complex in tetrahydrofuran solution [1.08M BH3-THF in THF (92.6 mL, 100 mmol)] was added thereto, and the mixture was stirred for three hours at 50° C. Subsequently, 1M hydrochloric acid was gradually added at 0° C., and the resultant mixture was stirred for one hour at room temperature. Thereafter, the reaction mixture was made basic with sodium carbonate. Tetrahydrofuran was evaporated, and then chloroform was added. Washing was performed sequentially with water and brine, followed by drying over sodium sulfate. The reaction mixture was subjected to concentration under reduced pressure and purification by silica gel column chromatography (chloroform/methanol=10/1), whereby the target compound was obtained (5.16 g, 13.02 mmol, 65.1%).

Workup

customTetrahydrofuran was evaporated
additionchloroform was added
washWashing
dry with materialby drying over sodium sulfate
concentrationThe reaction mixture was subjected to concentration under reduced pressure and purification by silica gel column chromatography (chloroform/methanol=10/1), whereby the target compound
customwas obtained (5.16 g, 13.02 mmol, 65.1%)

Sources & evidence

ORD record: ord-cf1e4c040663413cbf19a915c34dc627
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07109226B2

Reaction notes

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