3-Fluoropyrrolidine → HCID 58109584, compound

HRID 2037604Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C@@:13]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)([CH2:16][CH2:17]O)[O:12][C:11]2=[O:26])[CH3:9])=[CH:4][CH:3]=1.[F:27][C@@H:28]1[CH2:32][CH2:31][NH:30][CH2:29]1>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]([N:10]2[CH2:15][CH2:14][C@@:13]([C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)([CH2:16][CH2:17][N:30]3[CH2:31][CH2:32][C@@H:28]([F:27])[CH2:29]3)[O:12][C:11]2=[O:26])[CH3:9])=[CH:6][CH:7]=1

Participants

Reactant 2

HCID 27591633-Fluoropyrrolidine

HCID 58109626HCID 58109626, compound

Product 1

HCID 58109584HCID 58109584, compound

Procedure

The title compound was prepared from (S)-3-((S)-1-(4-bromophenyl)ethyl)-6-(4-fluorophenyl)-6-(2-hydroxyethyl)-1,3-oxazinan-2-one and (R)-3-fluoropyrrolidine following procedures analogous to those described in Example 178. LC-MS Method 2 tR=1.682 min, m/z=516.9; 1H NMR (CDCl3) 1.42 (d, 3H), 1.82-2.30 (m, 9H), 2.52-2.64 (m, 1H), 2.67-2.88 (m, 3H), 4.93-5.13 (m, 1H), 5.53 (m, 1H), 6.71 (d, 2H), 6.98 (m, 2H), 7.18 (m, 2H), 7.19 (m, 1H).

Sources & evidence

ORD record: ord-3885d38ac57d4d9baaf26de46e372d44
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575156B2

Reaction notes

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