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

HRID 1642192Notes

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-12f8c74d42d44401aa68b38de14b6369
Source dataset: uspto-grants-2012_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08119635B2

Reaction notes

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