tert-butyl N-(4-aminobutyl)carbamate → HCID 15314931, compound

HRID 1108651Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][NH2:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N1[C:23](=[O:24])[C:22]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:21]2[C:20]1=[O:29])(OCC)=O>O1CCOCC1>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][N:13]1[C:23](=[O:24])[C:22]2=[CH:25][CH:26]=[CH:27][CH:28]=[C:21]2[C:20]1=[O:29])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 52.5 °C

Procedure

5.41 g (28.74 mmol) of N-(tert-butoxycarbonyl)-1,4-diaminobutane was dissolved in 100 ml of 1,4-dioxane and 4.86 g (28.74 mmol) of N-carboethoxyphthalimide was added thereto. The mixture was heated at 45 to 60° C. and stirred for 4 hours. After the reaction mixture was concentrated under reduced pressure, 1N hydrochloric acid was added thereto and the resulting solution was extracted with ethyl acetate. The extract was washed with brine and dried (Na2SO4). The solvent was distilled off and the residue was purified by silica gel column chromatography (chloroform:methanol=200:1 (v/v)) to obtain 5.40 g (16.96 mmol) of N-[4-(tert-butoxycarbonylamino)butyl]phthalimide as a white solid. Its spectroscopic data are as follows:

Workup

concentrationAfter the reaction mixture was concentrated under reduced pressure, 1N hydrochloric acid
additionwas added
extractionthe resulting solution was extracted with ethyl acetate
washThe extract was washed with brine
dry with materialdried (Na2SO4)
distillationThe solvent was distilled off
customthe residue was purified by silica gel column chromatography (chloroform:methanol=200:1 (v/v))

Sources & evidence

ORD record: ord-452f47a9fdd547bcb7aa21e1159c01e5
Source dataset: uspto-grants-2000_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06069149

Reaction notes

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