Sodium Acetate → tert-Butyl 5-oxohexahydrocyclopenta(c)pyrrole-2(1H)-carboxylate

HRID 1477982Notes

Reaction equation

[C:1]([O:5][C:6]([N:8]1[CH2:12][CH:11]([CH2:13]C(O)=O)[CH:10]([CH2:17][C:18]([OH:20])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC([O-])=O.[Na+]>CC(OC(C)=O)=O>[O:20]=[C:18]1[CH2:13][CH:11]2[CH2:12][N:8]([C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:9][CH:10]2[CH2:17]1

Participants

Conditions

Temperature: 120 °C

Procedure

To a suspension of 2,2′-(1-(tert-butoxycarbonyl)pyrrolidine-3,4-diyl)diacetic acid (3.40 g, 11.8 mmol) in Ac2O (21 mL) was added NaOAc (0.78 g, 9.5 mmol) and the reaction mixture was stirred at 120° C. for 3 h. After that, the resulting mixture was cooled down to rt then filtered and washed with EtOAc (20 mL×2). The filtrate was concentrated in vacuo and the residue was purified by silica gel chromatography (EtOAc/PE (v/v)=1/4) to give the title compound as orange yellow oil (1.38 g, 55.0%).

Workup

temperatureAfter that, the resulting mixture was cooled down to rt
filtrationthen filtered
washwashed with EtOAc (20 mL×2)
concentrationThe filtrate was concentrated in vacuo
customthe residue was purified by silica gel chromatography (EtOAc/PE (v/v)=1/4)

Sources & evidence

ORD record: ord-7bb6b183fa5a46de970d5e6f0f23fa2b
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09403801B2

Reaction notes

Loading…