Tetrahydrofuran → (R)-1-[3-Amino-4-(benzyloxy)phenyl]-2-bromoethanol

HRID 385252Notes

Reaction equation

HRID 385252 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([OH:18])[CH2:16][Br:17])=[CH:11][C:10]=1[N+:19]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1COCC1>O=[Pt]=O.C1(C)C=CC=CC=1>[NH2:19][C:10]1[CH:11]=[C:12]([C@@H:15]([OH:18])[CH2:16][Br:17])[CH:13]=[CH:14][C:9]=1[O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 10882679(R)-1-(4-Benzyloxy-3-nitrophenyl)-2-bromoethanol

Product 1

HCID 11232489(R)-1-[3-Amino-4-(benzyloxy)phenyl]-2-bromoethanol

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 1140TolueneSolvent

Procedure

(R)-1-[4-(benzyloxy)-3-nitrophenyl]-2-bromoethanol (0.200 g, 0.569 mmol) in 1:1 THF:toluene (5 mL) was reacted with 1% (w/w) PtO2 on a Parr shaker at 45 psi at rt overnight. The next morning the PtO2 was removed by filtration over celite. The product was concentrated to give the title compound. ES/MS calcd. for C15H17BrNO2+ 322.0. found m/z=322 (M+H)+.

Workup

  1. customThe next morning the PtO2 was removed by filtration over celite
  2. concentrationThe product was concentrated

Sources & evidence

ORD record
ord-a27968119bc342858691d38e2e7b16c4
Source dataset
uspto-grants-2013_02
Patent number
US08367829B2

Reaction notes

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