Trifluoroacetic acid → (3s,6r,7As)-6-amino-5-oxohexahydropyrrolizine-3-carbonitrile trifluoroacetate

HRID 10426

Reaction equation

HRID 10426 reaction equation
[C:1]([C@@H:3]1[CH2:10][CH2:9][C@@H:8]2[N:4]1[C:5](=[O:19])[C@H:6]([NH:11]C(=O)OC(C)(C)C)[CH2:7]2)#[N:2].C1(SC)C=CC=CC=1.[F:28][C:29]([F:34])([F:33])[C:30]([OH:32])=[O:31]>>[F:28][C:29]([F:34])([F:33])[C:30]([OH:32])=[O:31].[NH2:11][C@@H:6]1[CH2:7][C@H:8]2[N:4]([C@H:3]([C:1]#[N:2])[CH2:10][CH2:9]2)[C:5]1=[O:19]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7520ThioanisoleHCID 91321587Tert-butyl ((2r,5s,7as)-5-cyano-3-oxohexahydropyrrolizin-2-yl)carbamate

Product 1

HCID 11357934(3s,6r,7As)-6-amino-5-oxohexahydropyrrolizine-3-carbonitrile trifluoroacetate

Procedure

80 mg of tert-butyl ((2R,5S,7aS)-5-cyano-3-oxohexahydropyrrolizin-2-yl)carbamate were C reacted with 10% thioanisole in 1 ml of trifluoroacetic acid for 30 min. The solvents were then removed in vacuo, and the residue was stirred with diusopropyl ether.

Workup

  1. customThe solvents were then removed in vacuo

Sources & evidence

ORD record
ord-300496268f1a4ca7a2622d242dab1799
Source dataset
uspto-grants-2006_08
Patent number
US07094800B2

Linked notes

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