Acetic Acid → HCID 66723387, compound

Batch 1: NaBH(OAc)3 (271 mg, 1.28 mmol), HOAc (0.07 mL), and 2-Methylpyrrolidine (0.043 mL, 0.42 mmol) were added to a solution of (5-formyl-2-thienyl)boronic acid (100 mg, 0.64 mmol) in CH2Cl2 (4 mL) in a 2-dram vial. The vial was capped and the reaction was stirred at room temperature for 15 h. The reaction mixture was loaded directly onto a 2 g SCX cartridge (pre-equilibrated with MeOH), eluting in sequence with MeOH (12 mL) and a 2 M solution of NH3/MeOH (8 mL). The fractions containing the boronic acid crude product were concentrated under a stream of N2 and dried under high vacuum to give 45 mg of crude product. The crude product was taken up in saturated NaHCO3 (2 mL) and extracted with EtOAc (3×2 mL) to give 6.6 mg of crude {5-[(2-methyl-1-pyrrolidinyl)methyl]-2-thienyl}boronic acid.

1. customThe vial was capped
2. washeluting in sequence with MeOH (12 mL)
3. additionThe fractions containing the boronic acid crude product
4. concentrationwere concentrated under a stream of N2
5. customdried under high vacuum
6. customto give 45 mg of crude product
7. extractionextracted with EtOAc (3×2 mL)

ORD record

ord-4be0a9e83ac640c19748a206d7a084da

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08063071B2