Methanol → 3-Amino-3-(4-chlorophenyl)propan-1-ol

温度

0 °C

Borane-tetrahydrofuran complex (94.0 mL, 93.92 mmol) was added dropwise to a stirred suspension of 3-amino-3-(4-chlorophenyl)propionic acid (2.50 g, 12.52 mmol) in THF (75 mL) at 0° C. over a period of 20 minutes under nitrogen. The resulting suspension was stirred at 0° C. for 30 minutes then at 22° C. for 5 hours. The reaction mixture was added portionwise to methanol (500 mL). The mixture was concentrated, redissolved in methanol (250 mL) and reconcentrated (this process was repeated three times). The residue was dissolved in DCM (200 mL) and washed with 1N NaOH (150 mL). The aqueous layer was extracted with DCM (5×100 mL) and the extracts combined with the organic layer. The combined organics were washed with saturated brine (2×150 mL), dried over MgSO4 and concentrated to afford a white semi-solid. The crude product was purified by flash silica chromatography, elution gradient 5 to 7% (10:1 MeOH/conc. NH3 (aq)) in DCM. Pure fractions were evaporated to dryness to afford 3-amino-3-(4-chlorophenyl)propan-1-ol (1.320 g, 56.8%) as a white solid.

1. waitat 22° C. for 5 hours
2. concentrationThe mixture was concentrated
3. dissolutionredissolved in methanol (250 mL)
4. dissolutionThe residue was dissolved in DCM (200 mL)
5. washwashed with 1N NaOH (150 mL)
6. extractionThe aqueous layer was extracted with DCM (5×100 mL)
7. washThe combined organics were washed with saturated brine (2×150 mL)
8. dry with materialdried over MgSO4
9. concentrationconcentrated
10. customto afford a white semi-solid
11. customThe crude product was purified by flash silica chromatography, elution gradient 5 to 7% (10:1 MeOH/conc. NH3 (aq)) in DCM
12. customPure fractions were evaporated to dryness

ORDレコード

ord-86bbb29a1ac042cd89b6e1fee70c496a

出典データセット

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08101623B2