Chlorotrimethylsilane → (-)-β-Amino-4-iodobenzeneethanol

Temperature

0 °C

To a stirred solution of lithium borohydride in THF (25.1 ml, 2 M solution) under an argon atmosphere was added dropwise chlorotrimethylsilane (12.7 ml). To the resulting suspension was added portionwise (RS)-amino-(4-iodo-phenyl)-acetic acid hydrochloride (6.30 g). Stirring was continued for 4 h and then the mixture was cooled to 0° C. and quenched by dropwise addition of methanol (4.5 ml). After stirring for 15 min at room temperature, water was added and the mixture was then diluted with ethyl acetate. Saturated brine was then added and the aqueous phase made alkaline (pH 14) by addition of 5 N aq NaOH. The phases were separated and the organic phase was washed with saturated brine and then dried over sodium sulphate and concentrated in vacuo to afford (RS)-2-amino-2-(4-iodo-phenyl)-ethanol (5.27 g, quant.) as a yellow solid. MS (ISP): 264.1 ([M+H]+).

1. customquenched by dropwise addition of methanol (4.5 ml)
2. stirringAfter stirring for 15 min at room temperature
3. additionwater was added
4. additionthe mixture was then diluted with ethyl acetate
5. additionSaturated brine was then added
6. additionby addition of 5 N aq NaOH
7. customThe phases were separated
8. washthe organic phase was washed with saturated brine
9. dry with materialdried over sodium sulphate
10. concentrationconcentrated in vacuo

ORD record

ord-06cca349a9344eebb7444eeb671a1970

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08354441B2