(7R,8aS)-2-benzyloctahydropyrrolo[1,2-a]pyrazin-7-ol → (7R,8aS)-octahydropyrrolo[1,2-a]piperazin-7-ol

HRID 240426Notes

Reaction equation

HRID 240426 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]2[CH2:14][C@H:15]([OH:17])[CH2:16][C@H:10]2[CH2:9]1)C1C=CC=CC=1.[H][H]>[OH-].[OH-].[Pd+2].C(O)C>[CH2:9]1[NH:8][CH2:13][CH2:12][N:11]2[CH2:14][C@H:15]([OH:17])[CH2:16][C@@H:10]12

Participants

5

Reactant 2

HCID 14914621(7R,8aS)-2-benzyloctahydropyrrolo[1,2-a]pyrazin-7-olHCID 178418361HCID 178418361, compound

Product 1

HCID 53338751(7R,8aS)-octahydropyrrolo[1,2-a]piperazin-7-ol

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of (7R,8aS)-2-benzyloctahydropyrrolo[1,2-a]pyrazin-7-ol (Example 19D, 1 g, 4.30 mmol) and ethanol (10 mL) was added to 20% palladium hydroxide on carbon, wet (0.100 g) in a pressure bottle. The mixture was stirred at 50° C. for 16 hours under 30 psi of hydrogen. The mixture was filtered through a nylon membrane to give a crude intermediate (7R,8aS)-octahydropyrrolo[1,2-a]pyrazin-7-ol. The title compound was prepared according to the procedure described in Example 17E substituting (7R,8aS)-octahydropyrrolo[1,2-a]pyrazin-7-ol for (7S,8aR)-octahydropyrrolo[1,2-a]pyrazin-7-ol. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.43-1.58 (m, 2H), 1.97 (m, 2H), 2.10-2.35 (m, 3H), 2.90 (m, 1H), 3.20 (m, 1H), 3.62 (m, 1H), 3.77 (m, 1H), 4.14 (m, 1H), 4.80 (m, 1H), 7.92 (m, 2H), 8.10 (m, 2H); MS (ESI) m/z 351 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through a nylon membrane

Sources & evidence

ORD record
ord-131945253639413ebf43110dffda608a
Source dataset
uspto-grants-2014_02
Patent number
US08648074B2

Reaction notes

Loading…