Diisopropylethylamine → HCID 57544378, compound
Reaction equation
[NH2:1][CH2:2][CH:3]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:4][OH:5].C(N(C(C)C)CC)(C)C.Cl[C:22](Cl)([O:24]C(=O)OC(Cl)(Cl)Cl)Cl>C(Cl)Cl>[C:6]1([CH:3]2[CH2:4][O:5][C:22](=[O:24])[NH:1][CH2:2]2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A cooled (0° C.) solution of 3-amino-2-phenylpropan-1-ol (245 mg, 1.62 mmol) in CH2Cl2 (10 mL) was treated with diisopropylethylamine (1.65 mL, 9.72 mmol) and triphosgene (241 mg, 0.81 mmol), under an atmosphere of nitrogen. The reaction was stirred at 0° C. for an additional 2 h. The reaction was quenched with sat. NaHCO3 (2 mL) and then extracted with EtOAc (3×40 mL). The combined organic extracts were washed with brine (30 mL), dried (MgSO4), filtered and concentrated to afford the title compound as a colorless oil. LCMS=178.2 (M+1)+.
Workup
- customThe reaction was quenched with sat. NaHCO3 (2 mL)
- extractionextracted with EtOAc (3×40 mL)
- washThe combined organic extracts were washed with brine (30 mL)
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-b9980d380a11469fa2c7b5bccf5ace9e
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08865707B2
Reaction notes
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