Diisopropylethylamine → HCID 11446836, compound

To a solution of commercially available (2S,3aS,6aS)-benzyl octahydrocyclopenta[b]pyrrole-2-carboxylate hydrochloride (4.70 g, 16.68 mmol) in methylene chloride (42 mL) was added Di-tert-butyl dicarbonate (7.28 g, 33.36 mmol), N,N-diisopropylethylamine (5.82 mL, 33.36 mmol) and 4-(Dimethylamino)pyridine (0.20 g, 1.67 mmol). The solution was stirred under air for 16 hours. Upon completion, the reaction was concentrated in vacuo, diluted in ethyl acetate, and washed with 1N HCl. The aqueous layers were backextracted twice with ethyl acetate and the combined organic layers were dried over sodium sulfate, filtered and concentrated. The resulting residue was purified by silica gel chromatography (5-40% ethyl acetate in hexanes) to afford (2S,3aS,6aS)-1-tert-butoxycarbonyl)octahydrocyclopenta[b]pyrrole-2-carboxylic acid which was used without further purification. MS (ESI) m/z 368.47 [M+Na]+.

1. concentrationUpon completion, the reaction was concentrated in vacuo
2. additiondiluted in ethyl acetate
3. washwashed with 1N HCl
4. dry with materialthe combined organic layers were dried over sodium sulfate
5. filtrationfiltered
6. concentrationconcentrated
7. customThe resulting residue was purified by silica gel chromatography (5-40% ethyl acetate in hexanes)

ORD record

ord-7d7172a291c54c55940be3820faad7cf

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08575135B2