Tetrahydrofuran → (1S)-1-(3-amino-4-benzyloxyphenyl)-2-bromoethan-1-ol

HRID 1922290Notes

Reaction equation

HRID 1922290 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C@H:18]([OH:21])[CH2:19][Br:20])[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)([O-])=O.C1COCC1>C1(C)C=CC=CC=1>[NH2:1][C:4]1[CH:5]=[C:6]([C@H:18]([OH:21])[CH2:19][Br:20])[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 29944564(S)-1-(4-Benzyloxy-3-nitrophenyl)-2-bromoethanol

Product 1

HCID 59303911(1S)-1-(3-amino-4-benzyloxyphenyl)-2-bromoethan-1-olYield 69.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of the product of Step A) (18.7 g, 53.1 mmol) in toluene (40 mL) and THF (40 mL) was added to a Parr shaker bottle containing Pt2O (370 mg). This mixture was shaken under H2 (50 psi, 344.74 kpa) until the reaction was complete (18 h). The catalyst was removed by filtration, and the filtrate was concentrated to an oil. Column chromatography (1 kg silica gel packed in and eluted with CH2Cl2/MeOH, 19:1) gave 11.9 g (69.6%) of the title compound.

Workup

  1. custom(18 h)
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate was concentrated to an oil
  4. washColumn chromatography (1 kg silica gel packed in and eluted with CH2Cl2/MeOH, 19:1)

Sources & evidence

ORD record
ord-b7e97f47b5524d76b496bf3590dde497
Source dataset
uspto-grants-2012_05
Patent number
US08173829B2

Reaction notes

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