Chlorotrimethylsilane → beta-Amino-3-chlorobenzeneethanol
Reaction equation
[BH4-].[Li+].Cl[Si](C)(C)C.[NH2:8][CH:9]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=1)[C:10](O)=[O:11]>C1COCC1>[NH2:8][CH:9]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=1)[CH2:10][OH:11]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a stirred solution of lithium borohydride in THF (10.5 ml, 2 M solution) under an argon atmosphere was added dropwise chlorotrimethylsilane (5.34 ml). The resulting suspension was cooled to 0° C. and amino-(3-chlorophenyl)-acetic acid (2.0 g) was added portionwise. The ice bath was removed and stirring at r.t. was then continued for 16 h. The mixture was quenched by dropwise addition of methanol (15 ml) and then concentrated in vacuo. The residue was suspended in ethyl acetate and washed with 2 N aq NaOH. The phases were separated and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over sodium sulphate and concentrated in vacuo to afford (RS)-2-amino-2-(3-chloro-phenyl)-ethanol (1.84 g, quant.) as a yellow viscous oil. MS (ISP): 174.2 ([{37Cl}M+H]+), 172.2 ([{35Cl}M+H]+).
Workup
- customThe ice bath was removed
- customThe mixture was quenched by dropwise addition of methanol (15 ml)
- concentrationconcentrated in vacuo
- washwashed with 2 N aq NaOH
- customThe phases were separated
- extractionthe aqueous phase was extracted with ethyl acetate
- dry with materialThe combined organic phases were dried over sodium sulphate
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-f8fe01c88dce4940b5387a139f0f98a5
- Source dataset
- uspto-grants-2013_12
- Patent number
- US08604061B2
Reaction notes
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