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

HRID 2251457Notes

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-9feab623e6b04d0e907b66eba98ffa11
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07319106B2

Reaction notes

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