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

HRID 712452

反応式

HRID 712452 の反応式
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([N:14]1[C:22](=O)[CH:21]2[CH:16]([NH:17][CH2:18][CH2:19][CH2:20]2)[C:15]1=O)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1COCC1>[CH2:7]([N:14]1[CH2:22][CH:21]2[CH:16]([NH:17][CH2:18][CH2:19][CH2:20]2)[CH2:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

参加物

4

反応物 2

HCID 9899604Tetrahydro-6-(phenylmethyl)-1H-pyrrolo(3,4-b)pyridine-5,7(2H,6H)-dioneHCID 21226445Aluminium lithium hydride

生成物 1

HCID 113563766-Benzyloctahydro-1H-pyrrolo[3,4-b]pyridine収率 56.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of LiAlH4 (1.20 g) in THF was added slowly 6-benzyltetrahydro-1H-pyrrolo[3,4-b]pyridine-5,7(6H,7aH)-dione (3.00 g) at 0° C. The reaction mixture was refluxed for 6 h under N2, and then cooled to rt. The reaction mixture was quenched with water at 0° C. and filtered. The filtrate was concentrated in vacuo and the residue was chromatographed with a silica gel column (eluting agent: 10:1 (v/v) EA/MeOH) to give the title compound as yellow oil (1.50 g, 47.00%), HPLC: 90.00%. The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 217.1 (M+1); 1H NMR (400 MHz, CDCl3) δ: 1.49-1.50 (m, 2H), 1.63-1.66 (m, 2H), 2.76-2.88 (m, 2H), 1.90 (s, 1H), 2.17-2.19 (m, 1H), 2.52-2.63 (m, 4H), 2.74 (t, J=10.4 Hz, 1H), 2.81-2.84 (m, 1H), 2.95-2.98 (m, 1H), 3.21-3.22 (m, J=4.0 Hz), 3.66 (q, J=12.6 Hz, 1H), 7.22-7.34 (m, 5H) ppm.

後処理

  1. temperatureThe reaction mixture was refluxed for 6 h under N2
  2. customThe reaction mixture was quenched with water at 0° C.
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was chromatographed with a silica gel column (eluting agent: 10:1 (v/v) EA/MeOH)

出典と根拠

ORDレコード
ord-39e110ae568e46c7be9b6df1e3305345
出典データセット
uspto-grants-2015_11
特許番号
US09181277B2

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