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

HRID 393814Notes

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-fa9ba31c519d43f291330d99cd0c08c0
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06809105B2

Reaction notes

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