Trifluoroacetic acid → (3aS,6aS)-1-(5-hydroxy-3-pyridinyl)octahydropyrrolo[3,4-b]pyrrole

HRID 1817022Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:12][CH2:11][C@H:10]3[CH2:13][N:14](C(OC(C)(C)C)=O)[CH2:15][C@@H:9]23)[CH:5]=[N:6][CH:7]=1.FC(F)(F)C(O)=O>>[OH:1][C:2]1[CH:3]=[C:4]([N:8]2[CH2:12][CH2:11][C@H:10]3[CH2:13][NH:14][CH2:15][C@@H:9]23)[CH:5]=[N:6][CH:7]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 66757796tert-butyl (3aS,6aS)-1-(5-hydroxy-3-pyridinyl)hexahydropyrrolo[3,4-b]pyrrole-5(1H)-carboxylate

Product 1

HCID 9990536(3aS,6aS)-1-(5-hydroxy-3-pyridinyl)octahydropyrrolo[3,4-b]pyrroleYield 38%

Procedure

The product of Example 82B (3.21 mmol) and trifluoroacetic acid was processed according to the procedure described in Example 64C to provide the title compound (0.250 g, 1.22 mmol, 38% yield over two steps). MS (DCI/NH3) m/z 206 (M+H)+.

Sources & evidence

ORD record: ord-88433cde3587416489861f70bd56d2d0
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07598236B2

Reaction notes

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