Hydrochloric Acid → tert-Butyl 2-[2-(2-aminoethyl)phenoxy]-2-methylpropionate

HRID 350838Notes

Reaction equation

[NH2:1][C:2]([CH2:4][C:5]1[CH:21]=[CH:20][CH:19]=[CH:18][C:6]=1[O:7][C:8]([CH3:17])([CH3:16])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=O.Cl.C(N)C.C(OCC)(=O)C>O1CCCC1>[NH2:1][CH2:2][CH2:4][C:5]1[CH:21]=[CH:20][CH:19]=[CH:18][C:6]=1[O:7][C:8]([CH3:16])([CH3:17])[C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10]

Participants

Conditions

Temperature: 50 °C

Procedure

tert-Butyl 2-[2-(aminocarbonylmethyl)phenoxy]-2-methylpropionate (1.4 g, 4.87 mmol) was dissolved in tetrahydrofuran (5.0 mL). Subsequently, under nitrogen atmosphere, borane-THF complex in THF solution [1,0M BH3-THF in THF (14.6 mL, 14.6 mmol)] was added thereto, the mixture was stirred for three hours at 50° C. Thereafter, concentrated hydrochloric acid was gradually added thereto at 0° C. The resultant mixture was stirred for one hour at room temperature and made basic with an aqueous ethylamine solution. Ethyl acetate was added thereto. The mixture was sequentially washed with water and brine, followed by drying over sodium sulfate. The mixture was subjected to concentration under reduced pressure and purification by silica gel column chromatography (chloroform/methanol=30/1), whereby the target compound was obtained (830 mg, 2.97 mmol, 61%).

Workup

customat 0° C
washThe mixture was sequentially washed with water and brine
dry with materialby drying over sodium sulfate
concentrationThe mixture was subjected to concentration under reduced pressure and purification by silica gel column chromatography (chloroform/methanol=30/1), whereby the target compound
customwas obtained (830 mg, 2.97 mmol, 61%)

Sources & evidence

ORD record: ord-a0cf2c56be154994939d38a77f893097
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07183295B2

Reaction notes

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