Hydrochloric Acid → HCID 68525020, compound

HRID 1836584Notes

Reaction equation

HRID 1836584 reaction equation
[CH2:1]([N:8]1[CH2:20][C@H:19]2[C@:10](C(OCC)=O)([C:11](=[O:23])[N:12]3[CH2:22][CH2:21][C:14]4[CH:15]=[CH:16][CH:17]=[C:18]2[C:13]3=4)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>O1CCOCC1>[CH2:1]([N:8]1[CH2:20][C@H:19]2[C@H:10]([C:11](=[O:23])[N:12]3[CH2:22][CH2:21][C:14]4[CH:15]=[CH:16][CH:17]=[C:18]2[C:13]3=4)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 131724542HCID 131724542, compound

Product 1

HCID 68525020HCID 68525020, compoundYield 97.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of (±)-cis ethyl 9-benzyl-7-oxo-4,5,8,9,10,10a-hexahydrodipyrrolo[3,4-c:3′,2′,1′-ij]quinoline-7a(7H)-carboxylate (3.9 g, 10.4 mmol) in 50 mL of 1,4-dioxane was added 50 mL of 3N HCl and the resulting mixture was stirred at 100° C. for 24 h. The dioxane and most of the water was removed in vacuo, and the residue was basified with sat'd aq Na2CO3 and extracted with ethyl acetate. The layers were separated and the organics were washed with brine, dried (MgSO4), filtered through a pad of silica gel and concentrated to afford 3.1 g (96%) of (±)-cis-9-benzyl-4,5,8,9,10,10a-hexahydrodipyrrolo[3,4-c:3′,2′,1′-ij]quinolin-7(7aH)-one free base, which was sufficiently pure to be used without purification. LRMS (ES)+: 305.1 (M+H)+. A portion of this material (50 mg, 0.16 mmol) was dissolved in 5 mL of ether and 1 mL of absolute ethanol. Then there was added 2M HCl in ether (0.165 mL, 0.33 mmol). The resulting solid was filtered, washed twice with ether and dried in vacuo to afford the title compound of EXAMPLE 107 as a pale yellow powder. 1H NMR (dmso-D6) δ: 7.60-7.50 (m, 2H), 7.48-7.38 (m, 3H), 7.19-7.15 (m, 1H), 7.12-7.07 (m, 1H), 6.98-6.90 (m, 1H), 4.45-4.37 (m, 1H), 4.30-4.18 (m, 1H), 4.02-3.90 (m, 2H), 3.87-3.77 m, 2H), 3.68-3.40 (m, 3H), 3.21-3.05 (m, 3H). LRMS (ES)+: 305.1 (M+H)+.

Workup

  1. customThe dioxane and most of the water was removed in vacuo
  2. extractionextracted with ethyl acetate
  3. customThe layers were separated
  4. washthe organics were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered through a pad of silica gel
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0df28dcbb58f4805a2d96c42b92f233c
Source dataset
uspto-grants-2004_08
Patent number
US06777406B2

Reaction notes

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