Cycloheptanone → Ethyl 3-methyl-1,4,5,6,7,8-hexahydrocyclohepta[b]pyrrole-2-carboxylate

HRID 1596530Notes

Reaction equation

C1(N[N:8]=[C:9]([C:15](=O)[CH3:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])C=CC=CC=1.C([O-])(=O)C.[Na+].[C:23]1(=O)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1>C(O)(=O)C.[Zn]>[CH3:16][C:15]1[C:23]2[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][C:24]=2[NH:8][C:9]=1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

Conditions

Temperature: 80 °C

Procedure

Ethyl 2,3-dioxobutanoate-2-phenylhydrazone (20.9 g) (T. D; Lash et al., J. Org. Chem. 1992, 57, 4809-4820) in acetic acid (50 ml) was added dropwise to a stirred solution of sodium acetate (10 g), and cycloheptanone (10 g) in acetic acid (100 ml) at 60° C. over 30 minutes. Throughout the addition, small portions of zinc dust (30 g) were added. The reaction was stirred for an additional hour at 80° C., then poured into ice-water (500 g). The resulting solid precipitate was filtered and recrystallised from ethanol to give the product as white needles (2.77 g, 14%), NMR d(CDCl3) 1.38 (3H, t), 1.60-1.95 (6H, m), 2.24 (3H, s), 2.48 (2H, t), 2.68 (2H, t), 4.30 (2H, q), 8.70 (111, bs); M/z (+) 222 (MH+), 176.

Workup

additionwere added
filtrationThe resulting solid precipitate was filtered
customrecrystallised from ethanol

Sources & evidence

ORD record: ord-fec11e9670754589956ab616c4a58ad7
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06291507B1

Reaction notes

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