1,4-Dioxane → trans-5a',6',7',8',9',9a'-hexahydro-5'H-spiro[piperidine-4,4'-pyrrolo[1,2-a]quinoxaline]

HRID 1405338Notes

Reaction equation

HRID 1405338 reaction equation
[CH:1]1[N:5]2[C@H:6]3[C@H:11]([NH:12][C:13]4([CH2:18][CH2:17][N:16](C(OC(C)(C)C)=O)[CH2:15][CH2:14]4)[C:4]2=[CH:3][CH:2]=1)[CH2:10][CH2:9][CH2:8][CH2:7]3.O1CCOCC1>Cl>[CH:1]1[N:5]2[C@H:6]3[C@H:11]([NH:12][C:13]4([CH2:14][CH2:15][NH:16][CH2:17][CH2:18]4)[C:4]2=[CH:3][CH:2]=1)[CH2:10][CH2:9][CH2:8][CH2:7]3

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 131732186trans-tert-butyl 5a',6',7',8',9',9a'-hexahydro-5'H-spiro[piperidine-4,4'-pyrrolo[1,2-a]quinoxaline]-1-carboxylate

Product 1

HCID 68175043trans-5a',6',7',8',9',9a'-hexahydro-5'H-spiro[piperidine-4,4'-pyrrolo[1,2-a]quinoxaline]

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

trans-tert-Butyl 5a′,6′,7′,8′,9′,9a′-hexahydro-5′H-spiro[piperidine-4,4′-pyrrolo[1,2-a]quinoxaline]-1-carboxylate (0.311 g, 0.901 mmol) was suspended in hydrogen chloride in dioxane (2.0 mL of 4.0 M, 8.0 mmol). The reaction mixture was allowed to stand for 2 hours. The reaction mixture was then evaporated to dryness to give trans-5a′,6′,7′,8′,9′,9a′-hexahydro-5′H-spiro[piperidine-4,4′-pyrrolo[1,2-a]quinoxaline]. ESI-MS m/z calc. 245.2, found 246.3 (M+1)+; Retention time: 0.32 minutes (3 min run).

Workup

  1. customThe reaction mixture was then evaporated to dryness

Sources & evidence

ORD record
ord-3c874922106546ea907a7ae624fb48c1
Source dataset
uspto-grants-2014_12
Patent number
US08916565B2

Reaction notes

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