Acetic Acid → HCID 22956547, compound

To a stirred solution of trans-4-amino-1-tert-butoxycarbonyl-(2S)-tert-butyldiphenylsilyloxy) methylpyrrolidine (400 mg, 0.88 mmol), AcOH (120 ml, 2.0 mmol), and 37% HCHO aq (500 ml) in MeOH (10 ml) was added NaBH3CN (111 mg, 1.76 mmol) at 0° C. The reaction mixture was stirred at room temperature for 18 hr. After concentrated in vacuo, water was added and extracted with CH2Cl2. The extract was dried over Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography on silica gel with MeOH—CH2Cl2 (3:97, v/v) as eluent to give trans-1-tert-butoxycarbonyl-(2S)-tert-butyldiphenylsilyloxy)methyl-4-dimethylaminopyrrolidine (330 mg, 78%) as a pale yellow oil. 1H-NMR (CDCl3) δ1.06 (s, 9H), 1.33 and 1.45 (each s total 9H), 1.80-2.25 (m, 2H), 2.23 (br s, 6H), 2.95-4.05 (m, 6H), 7.36-7.39 (m, 6H), 7.63-7.65 (m, 4H).

1. concentrationAfter concentrated in vacuo, water
2. additionwas added
3. extractionextracted with CH2Cl2
4. dry with materialThe extract was dried over Na2SO4
5. concentrationconcentrated in vacuo
6. customThe residue was purified by column chromatography on silica gel with MeOH—CH2Cl2 (3:97

ORD record

ord-3d4ab539be4f445ebfa8a8b6fc6e1e4c

Source dataset

uspto-grants-2004_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06756378B2