tert-Butyl isocyanoacetate → tert-Butyl (S)-12,12a-dihydroimidazo[1,5-a]pyrrolo[2, 1-c]quinoxaline-1-carboxylate

HRID 1899952Notes

Reaction equation

HRID 1899952 reaction equation
[C:1]1(=O)[N:5]2[C:6]3[C:11]([NH:12][C:13](=O)[C@@H:4]2[CH2:3][CH2:2]1)=[CH:10][CH:9]=[CH:8][CH:7]=3.[N+:16]([CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])#[C-:17]>>[C:18]1([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[N:16]=[CH:17][N:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[N:5]3[CH:1]=[CH:2][CH2:3][C@H:4]3[C:13]=12

Participants

3

Reactant 2

HCID 2759404tert-Butyl isocyanoacetateHCID 10104293(S)-3,3a-Dihydropyrrolo(1,2-a)quinoxaline-1,4(2H,5H)-dione

Product 1

HCID 53953867tert-Butyl (S)-12,12a-dihydroimidazo[1,5-a]pyrrolo[2, 1-c]quinoxaline-1-carboxylate

Procedure

Following the general procedure of EXAMPLE 30 and making non-critical variations but starting with (S)-3,3a-dihydropyrrolo[1,2-a]quinoxaline-1,4(2H,5H)-dione (intermediate formed in EXAMPLE 282, 0.638 g) and tert-butyl isocyanoacetate (0.621 g), the title compound is obtained, mp 202°-207° (decomp); MS (m/z) at 325; IR (mineral oil) 1719, 1363, 1700, 1507, 1161, 1293 cm-1 ; NMR (CDCl3) 1.64, 2.25-2.40, 2.55-2.81, 3.31-3.41, 5.26, 7.23-7.29, 7.33, 7.52, 8.06, 8.34 δ; [α]D =-248° (0.96, methanol).

Sources & evidence

ORD record
ord-04913cf4be094362a6920062d0d2ca05
Source dataset
uspto-grants-1996_11
Patent number
US05574038

Reaction notes

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