Trifluoroacetic acid → 6-Fluoro-2-methyl-3-((3R,9aS)-octahydropyrazino[2,1-c][1,4]oxazin-3-yl)benzonitrile 2,2,2-trifluoroacetate

HRID 2175891Notes

Reaction equation

[C:1]([C:3]1[C:4]([CH3:27])=[C:5]([C@H:10]2[O:15][CH2:14][C@@H:13]3[CH2:16][N:17](C(OC(C)(C)C)=O)[CH2:18][CH2:19][N:12]3[CH2:11]2)[CH:6]=[CH:7][C:8]=1[F:9])#[N:2].[C:28]([OH:34])([C:30]([F:33])([F:32])[F:31])=[O:29]>>[F:31][C:30]([F:33])([F:32])[C:28]([OH:34])=[O:29].[F:9][C:8]1[C:3]([C:1]#[N:2])=[C:4]([CH3:27])[C:5]([C@H:10]2[O:15][CH2:14][C@@H:13]3[CH2:16][NH:17][CH2:18][CH2:19][N:12]3[CH2:11]2)=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 71273580tert-butyl(3R,9aS)-3-(3-cyano-4-fluoro-2-methylphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate

Product 1

HCID 867270916-Fluoro-2-methyl-3-((3R,9aS)-octahydropyrazino[2,1-c][1,4]oxazin-3-yl)benzonitrile 2,2,2-trifluoroacetate

Procedure

tert-Butyl (3R,9aS)-3-(3-cyano-4-fluoro-2-methylphenyl)hexahydropyrazino[2,1-c][1,4]oxazine-8(1H)-carboxylate (1.73 g, 4.61 mmol) was treated with 10 mL TFA at RT for 1 h. The trifluoroacetic acid was then removed under reduced pressure to yield the title compound. LC-MS: M+1=276: 1H-NMR (600 MHz, DMSO) δ ppm 7.724 (dd, J=9.0, 6.2 Hz, 1H), 7.353 (t, J=8.85 Hz, 1H), 4.738 (d, J=10.3 Hz, 1H), 3.924 (d, J=11.10 Hz, 1H), 3.386 (t, J=11.65 Hz, 1H), 3.285 (d, J=12.3 Hz, 1H), 3.20 (d, J=11.8 Hz, 1H), 3.01 (b, 1H), 2.934 (d, J=11.6 Hz, 1H), 2.884 (d, J=11.0 Hz, 1H), 2.642 (b, 1H), 2.476 (s, 3H), 2.47 (b, 1H), 2.329-2.367 (m, 1H), 2.054-2.089 (m, 1H).

Workup

customThe trifluoroacetic acid was then removed under reduced pressure

Sources & evidence

ORD record: ord-1a5e109b5f144ae597b03dca5019e4b8
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09062070B2

Reaction notes

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