Water → Tetrahydro-6-(phenylmethyl)-1H-pyrrolo(3,4-b)pyridine-5,7(2H,6H)-dione

HRID 712451

Reaction equation

[CH2:1]([N:8]1[C:16](=[O:17])[C:15]2[C:10](=[N:11][CH:12]=[CH:13][CH:14]=2)[C:9]1=[O:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O>COCCO.[Pd]>[CH2:1]([N:8]1[C:16](=[O:17])[CH:15]2[CH:10]([NH:11][CH2:12][CH2:13][CH2:14]2)[C:9]1=[O:18])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 6-benzyl-5H-pyrrolo[3,4-b]pyridine-5,7(6H)-dione (5.00 g) in glycol monomethyl ether was added a catalytic amount of 10% Pd/C. The reaction mixture was heated to 90° C. and stirred for 6 h under H2, then cooled to rt. The resulted mixture was poured into 100 mL of water and extracted with CH2Cl2 (50 mL×3). The combined organic phases were dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 1:2 (v/v) PE/EA) to give the title compound as colorless oil (3.00 g, 60.00%), HPLC: 95.00%. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 245.1 (M+1); 1H NMR (400 MHz, CDCl3) δ: 1.47-1.53 (m, 4H), 2.12 (s, 1H), 2.63-2.69 (m, 1H), 2.76-2.88 (m, 2H), 3.83 (d, J=8.2, 2H), 4.64 (s, 1H), 7.25-7.36 (m, 5H) ppm.

Workup

temperaturecooled to rt
extractionextracted with CH2Cl2 (50 mL×3)
dry with materialThe combined organic phases were dried over anhydrous Na2SO4
filtrationfiltered
concentrationThe filtrate was concentrated in vacuo
customthe residue was chromatographed with a silica gel column (eluting agent: 1:2 (v/v) PE/EA)

Sources & evidence

ORD record: ord-371f326cff5f42b990e6ff8984c86e89
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181277B2

Linked notes

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