HCID 86680437, compound → HCID 51919072, compound

HRID 1184570Notes

Reaction equation

HRID 1184570 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].FC(F)(F)CO>[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 86680437HCID 86680437, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 51919072HCID 51919072, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 64092,2,2-TrifluoroethanolSolvent

Procedure

A mixture of (7S,8aR)-2-benzyloctahydropyrrolo[1,2-a]pyrazin-7-ol (Example 65D, 5 g, 21.52 mmol) and 2,2,2-trifluoroethanol (50 mL) was added to 20% palladium hydroxide on carbon, wet (0.500 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 (7S,8aR)-octahydropyrrolo[1,2-a]pyrazin-7-ol. The title compound was prepared according to the procedure described in Example 61 substituting (7S,8aR)-octahydropyrrolo[1,2-a]pyrazin-7-ol for (7R,8aS)-octahydropyrrolo[1,2-a]pyrazin-7-ol. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.43-1.63 (m, 2H), 2.10-2.27 (m, 3H), 2.50 (m, 1H), 2.80-3.00 (m, 2H), 3.20-3.50 (m, 2H), 4.22 (m, 1H), 4.42-4.60 (m, 1H), 4.80 (m, 1H), 7.70 (m, 3H), 7.82 (m, 1H); MS (ESI) m/z 315 (M+H)+.

Workup

  1. filtrationThe mixture was filtered through a nylon membrane

Sources & evidence

ORD record
ord-dfb6f63527f34d64acbe7e87efe80b7f
Source dataset
uspto-grants-2014_03
Patent number
US08669255B2

Reaction notes

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