Water → (R)-2-Amino-1-(3-chlorophenyl)ethanol

HRID 595802Notes

Reaction equation

HRID 595802 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[CH2:10][O:9]2)[CH:5]=[CH:6][CH:7]=1.C[Si]([N-:15][Si](C)(C)C)(C)C.[Na+].O>C1COCC1>[NH2:15][CH2:10][C@@H:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=1)[OH:9]

Participants

5

Reactant 3

HCID 962WaterHCID 2724254Sodium bis(trimethylsilyl)amideHCID 10898919(R)-(+)-3-Chlorostyrene oxide

Product 1

HCID 9920489(R)-2-Amino-1-(3-chlorophenyl)ethanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (R)-2-(3-chlorophenyl)oxirane (13 g, 84 mmol) in THF (84 mL) was added NaHMDS (1 M in THF) (252 mL, 252 mmol) slowly at 0° C. The reaction mixture was warmed up to room temperature and stirred for overnight. To the reaction mixture, water (33 mL, 2.5 mL/g) added. After stirring for 5 h at room temperature, solvent was removed in vacuo to about ¼ and partitioned by DCM. The bottom layer is a little cloudy and the top layer was a brown solution. Both layers were concentrated, which contained the desired (R)-2-amino-1-(3-chlorophenyl)ethanol (14 g, 97%). The combined products were used in next step without further purification. LCMS (m/z): 172.1 (MH+), 0.37 min.

Workup

  1. stirringAfter stirring for 5 h at room temperature
  2. customsolvent was removed in vacuo to about ¼
  3. custompartitioned by DCM
  4. concentrationBoth layers were concentrated
  5. customThe combined products were used in next step without further purification
  6. custom172.1 (MH+), 0.37 min.

Sources & evidence

ORD record
ord-7052e5797c044e11937ebf22e97f7309
Source dataset
uspto-grants-2016_01
Patent number
US09242996B2

Reaction notes

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