Hydrochloric Acid → tert-butyl N-(3-(3-hydroxypropyl)phenyl)carbamate

HRID 1978396Notes

Reaction equation

HRID 1978396 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[C:11]([O:15][C:16]([NH:18][C:19]1[CH:20]=[C:21]([CH2:25][CH2:26][C:27](OCC)=[O:28])[CH:22]=[CH:23][CH:24]=1)=[O:17])([CH3:14])([CH3:13])[CH3:12].Cl>O1CCCC1>[C:11]([O:15][C:16]([NH:18][C:19]1[CH:20]=[C:21]([CH2:25][CH2:26][CH2:27][OH:28])[CH:22]=[CH:23][CH:24]=1)=[O:17])([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21225700DiisobutylaluminumhydrideHCID 21994062Ethyl 3-(3-tert-butoxycarbonylaminophenyl)propionate

Product 1

HCID 21993723tert-butyl N-(3-(3-hydroxypropyl)phenyl)carbamateYield 40.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Diisobutylaluminium hydride (1.5 M in toluene, 57.0 ml, 85.5 mmol) was added dropwise to a stirred solution of ethyl 3-(3-tert-butoxycarbonylaminophenyl)propionate (9.35 g, 31.9 mmol) in tetrahydrofuran (100 ml) at 0° C. and the mixture was stirred at room temperature for 24 hours. 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 (2:1) to give 3-(3-tert-butoxycarbonylaminophenyl)propanol as a colorless oil (3.24 g, 40%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was successively washed with water saturated aqueous NaHCO3 and brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed on silica gel (100 g) with hexane-ethyl acetate (2:1)

Sources & evidence

ORD record
ord-a7680fa71dee469eaa7ce71a5aa4a2e4
Source dataset
uspto-grants-2001_05
Patent number
US06235731B1

Reaction notes

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