(S)-6-allyl-3-((2S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one → 3-((2S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-6-(2-hydroxyethyl)-1,3-oxazinan-2-one

HRID 403581Notes

Reaction equation

HRID 403581 reaction equation
C([C@]1(C2C=CC(F)=CC=2)OC(=O)N([C@H](C(C)(C)C)C)CC1)C=C.[CH3:24][C:25]([CH3:46])([CH3:45])[C@@H:26]([N:28]1[CH2:33][CH2:32][C@:31]([C:37]2[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=2)([CH2:34][CH2:35][OH:36])[O:30][C:29]1=[O:44])[CH3:27]>>[CH3:45][C:25]([CH3:24])([CH3:46])[C@@H:26]([N:28]1[CH2:33][CH2:32][C:31]([C:37]2[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=2)([CH2:34][CH2:35][OH:36])[O:30][C:29]1=[O:44])[CH3:27]

Participants

3

Reactant 2

HCID 67446212(S)-6-allyl-3-((2S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-1,3-oxazinan-2-oneHCID 67449856(R)-3-((S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-6-(2-hydroxyethyl)-1,3-oxazinan-2-one

Product 1

HCID 426422843-((2S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-6-(2-hydroxyethyl)-1,3-oxazinan-2-one

Procedure

(S)-6-allyl-3-((2S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one [Isomer 2] (500 mg, 1.57 mmol) was converted to (R)-3-((S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-6-(2-hydroxyethyl)-1,3-oxazinan-2-one [Isomer 2] (300 mg, 59%) following a procedure analogous to that described immediately above. LC-MS Method 1 tR=1.112, min, m/z=324.2; 1H NMR (CDCl3): 0.85-0.99 (m, 12H), 2.09-2.18 (m, 1H), 2.19-2.34 (m, 3H), 2.73-2.84 (m, 1H), 3.12-3.28 (m, 1H), 3.48-3.57 (m, 1H), 3.69-3.76 (m, 1H), 4.26-4.35 (m, 1H), 7.02-7.08 (m, 2H), 7.24-7.32 (m, 2H).

Sources & evidence

ORD record
ord-ffada3caac9f42c9bb6303478b97866b
Source dataset
uspto-grants-2014_06
Patent number
US08748444B2

Reaction notes

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