HCID 19433401, compound → 1,1-Dimethylethyl N-[3-(2-hydroxyphenyl)propyl]carbamate

HRID 1736615Notes

Reaction equation

HRID 1736615 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[O:18]CC1C=CC=CC=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd].C(O)C>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[OH:18])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 19433401HCID 19433401, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 194334151,1-Dimethylethyl N-[3-(2-hydroxyphenyl)propyl]carbamateYield 88.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4.64 g (14.1 mmol) of N-(tert-butoxycarbonyl)-3-[2-(benzyloxy)phenyl]propylamine, 1.0 g. of 5% palladium-on-carbon catalyst and 95 ml of ethanol was hydrogenated by shaking in a Parr apparatus using an initial pressure of 40 psi of hydrogen for 24 hours until hydrogen uptake was completed. The mixture was filtered and the filtrate was concentrated. The residue was chromatographed on a silica gel column which was eluted with a 5 to 20% gradient of ethyl acetate in hexane to give 3.14 g (88.7%) of the product as colorless crystals, mp 75°-77° C.

Workup

  1. customfor 24 hours
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customThe residue was chromatographed on a silica gel column which
  5. washwas eluted with a 5 to 20% gradient of ethyl acetate in hexane

Sources & evidence

ORD record
ord-216674f62fcf42d78a9cf144e0b47650
Source dataset
uspto-grants-1996_07
Patent number
US05541286

Reaction notes

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