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

HRID 1889225Notes

Reaction equation

HRID 1889225 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-d84e9a86b12a4fb1b6941c0e2c62e503
Source dataset
uspto-grants-2013_08
Patent number
US08501994B2

Reaction notes

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