Tetrahydrofuran → HCID 86711140, compound

HRID 624538Notes

Reaction equation

HRID 624538 reaction equation
[NH2:1][CH2:2][CH:3]1[N:8]([CH3:9])[CH2:7][CH2:6][N:5]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:4]1.[C:17](=[O:20])(O)[O-].[Na+].[CH:22]1N(C(O)=O)C=[C:25]2[C:30]=1[CH:29]=[CH:28][CH:27]=[CH:26]2.[O:34]1CCCC1>>[O:34]=[C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:17](=[O:20])[N:1]1[CH2:2][CH:3]1[N:8]([CH3:9])[CH2:7][CH2:6][N:5]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:4]1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 516892Sodium BicarbonateHCID 53780970HCID 53780970, compoundHCID 77474534tert-Butyl 3-(aminomethyl)-4-methylpiperazine-1-carboxylate

Product 1

HCID 86711140HCID 86711140, compound

Procedure

To a mixture of tert-butyl 3-(aminomethyl)-4-methylpiperazine-1-carboxylate, prepared as described in the previous step, (5.5 g, crude) and sodium bicarbonate (2.52 g, 30 mmol) in tetrahydrofuran (100 mL) was added a solution of 2H-isoindole-2-carboxylic acid, 1,3-dihydro-1,3-dioxo-, ethyl ester (6.59 g, 30 mmol) in tetrahydrofuran (20 mL) at ambient temperature. After stirring for 30 minutes, the suspension was filtered, and the filtrate was concentrated to give crude product which was purified by column chromatography to provide the title compound. 1H NMR (400 MHz, MeOD) δ 7.87-7.85 (m, 2H), 7.87-7.80 (m, 2H), 3.94-3.90 (m, 1H), 3.75-3.65 (br, 3H), 3.43-3.41 (br, 1H), 3.30-3.28 (m, 2H), 3.49 (s, 3H), 2.39-2.38 (m, 1H), 2.30-2.28 (m, 1H), 1.36 (s, 9H).

Workup

  1. customprepared
  2. filtrationthe suspension was filtered
  3. concentrationthe filtrate was concentrated
  4. customto give crude product which
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-d81f86653bfe4a758c5427c5553cf9a5
Source dataset
uspto-grants-2016_04
Patent number
US09303041B2

Reaction notes

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