Pyridine → Fmoc-4-aminobenzylalcohol

HRID 910754Notes

Reaction equation

HRID 910754 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][CH:3]=1.[C:10](Cl)([O:12][CH2:13][CH:14]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:20]2[C:15]1=[CH:16][CH:17]=[CH:18][CH:19]=2)=[O:11].N1C=CC=CC=1>C1COCC1.C(OCC)(=O)C>[CH:25]1[C:26]2[CH:14]([CH2:13][O:12][C:10](=[O:11])[NH:1][C:2]3[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][CH:3]=3)[C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:21]=2[CH:22]=[CH:23][CH:24]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 343679-Fluorenylmethyl chloroformateHCID 693314-Aminobenzyl alcohol

Product 1

HCID 64795261Fmoc-4-aminobenzylalcohol

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of (4-amino-phenyl)-methanol (500 mg), Fmoc-Cl (1.2 g) and pyridine (1 ml) in THF (15 ml) was stirred for 1 h. The reaction mixture was diluted with ethyl acetate and washed with water. The organic layer was separated, dried (MgSO4), filtered and concentrated in vacuo. The residue was recrystallized from dichloromethane. Yield: 470 mg. MS-ESI: [M+H]+=346.

Workup

  1. washwashed with water
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was recrystallized from dichloromethane

Sources & evidence

ORD record
ord-7563f540b6754a238eb7f293cb006d8e
Source dataset
uspto-grants-2011_09
Patent number
US08022218B2

Reaction notes

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