Ammonia → (1R)-benzyl 3-allyl-3-aminocyclopentanecarboxylate

To a solution of (R)-benzyl 3-oxocyclopentanecarboxylate (WO 2007092681, 1 g, 4.58 mmol) in methanol (5 mL) was added 2-allyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (1.155 g, 6.87 mmol) and ammonia (7N solution in MeOH, 8 mL). The resulting mixture was stirred at room temperature for 16 hours. The reaction mixture was concentrated and the residue was subjected to preparative HPLC(Shimadzu VP-ODS 20×100 mm, 8 min. gradient, Solvent A: 10% MeOH, 90% H2O, 0.1% TFA; Solvent B: 90% MeOH, 10% H2O, 0.1% TFA; wavelength: 220 nM). The desired fractions were collected, concentrated and partitioned between ethyl acetate (20 mL) and saturated aqueous sodium bicarbonate solution (10 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to yield (1R)-benzyl 3-allyl-3-aminocyclopentanecarboxylate (616 mg, 2.38 mmol, 52% yield). MS (ESI+) m/z 260 (M+H)+

1. concentrationThe reaction mixture was concentrated
2. customwas subjected to preparative HPLC(Shimadzu VP-ODS 20×100 mm, 8 min. gradient, Solvent A
3. customThe desired fractions were collected
4. concentrationconcentrated
5. custompartitioned between ethyl acetate (20 mL) and saturated aqueous sodium bicarbonate solution (10 mL)
6. dry with materialThe organic layer was dried over anhydrous Na2SO4
7. concentrationconcentrated under reduced pressure

ORD record

ord-6dda60c6e8984406ad736bcaf5f085a6

Source dataset

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08877749B2