Hydrochloric Acid → 3-(4-Tert-butoxycarbonylaminophenyl)propanol

HRID 1978392Notes

Reaction equation

[H-].C([Al+]CC(C)C)C(C)C.[C:11]([O:15][C:16]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][CH2:26][C:27](OCC)=[O:28])=[CH:21][CH:20]=1)=[O:17])([CH3:14])([CH3:13])[CH3:12].Cl>O1CCCC1>[C:11]([O:15][C:16]([NH:18][C:19]1[CH:20]=[CH:21][C:22]([CH2:25][CH2:26][CH2:27][OH:28])=[CH:23][CH:24]=1)=[O:17])([CH3:14])([CH3:13])[CH3:12]

Participants

Conditions

Temperature: 0 °C

Procedure

Diisobutylaluminium hydride(l.5 M in toluene, 30.5 ml, 45.8 mmol) was added dropwise to a stirred solution of ethyl 3-(4-tert-butoxycarbonylaminophenyl)propionate (6.10 g, 20.8 mmol) in tetrahydrofuran (60 ml) at 0° C. and the mixture was stirred at 0° C. for 1 hour. 2N-hydrochloric acid was added to the mixture and the mixture was extracted with ethyl acetate. The extract was successively washed with water, saturated aqueous NaHCO3 and brine, dried over MgSO4 and concentrated in vacuo. The residue was chromatographed on silica gel (100 g) with hexane-ethyl acetate (3:2) to give 3-(4-tert-butoxycarbonylaminophenyl)propanol as a colorless oil (2.66 g, 51%).

Workup

extractionthe mixture was extracted with ethyl acetate
washThe extract was successively washed with water, saturated aqueous NaHCO3 and brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo
customThe residue was chromatographed on silica gel (100 g) with hexane-ethyl acetate (3:2)

Sources & evidence

ORD record: ord-2707dce753ee478ba7fbac6412c6619f
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06235731B1

Reaction notes

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