3-(3-Bromophenyl)propanamide → 3-(3-Bromophenyl)propan-1-amine

To a solution of 3-(3-bromophenyl)propionamide (94) (4.5 g, 19.7 mmol) in THF (50 ml) under argon was added BH3-THF complex (39.4 mL of a 1.0 M solution in THF, 39.4 mmol) and the mixture was stirred at room temperature for 18 h. The reaction was quenched with the cautious addition of 6 M HCl to pH 1. After stirring 4 h the solution was adjusted to pH>10 with the addition of 50% aqueous NaOH. This aqueous solution was extracted with EtOAc. The combined organics were washed with brine, dried over Na2SO4 and concentrated under reduced pressure to give 3-(3-bromophenyl)propan-1-amine (95) as an oil. This material was used in the next synthetic step without purification. 1H NMR (400 MHz, DMSO-d6) δ 7.40 (s, 1H), 7.35 (dt, J=6.4, 2.4 Hz, 1H), 7.26 (br s, 1H), 7.18-7.24 (m, 2H), 6.75 (br s, 1H), 2.78 (t, J=7.6 Hz, 2H), 2.34 (t, J=7.6 Hz, 2H).

1. customThe reaction was quenched with the cautious addition of 6 M HCl to pH 1
2. stirringAfter stirring 4 h the solution
3. additionwas adjusted to pH>10 with the addition of 50% aqueous NaOH
4. extractionThis aqueous solution was extracted with EtOAc
5. washThe combined organics were washed with brine
6. dry with materialdried over Na2SO4
7. concentrationconcentrated under reduced pressure

ORDレコード

ord-08a834a0b0fe46a48ef40c9076665ca6

出典データセット

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08653142B2