(S)-3-((S)-1-(4-bromophenyl)ethyl)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-one → HCID 70652442, compound

HRID 1426044Notes

Reaction equation

HRID 1426044 reaction equation
CC1(C)C(C)(C)OB([C:9]2[N:14]=[C:13]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)[CH:12]=[CH:11][CH:10]=2)O1.Br[C:23]1[CH:28]=[CH:27][C:26]([C@@H:29]([N:31]2[CH2:36][CH2:35][C@:34]([CH2:43][C:44]([OH:47])([CH3:46])[CH3:45])([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[O:33][C:32]2=[O:48])[CH3:30])=[CH:25][CH:24]=1>>[OH:47][C:44]([CH3:45])([CH3:46])[CH2:43][C@@:34]1([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[O:33][C:32](=[O:48])[N:31]([C@H:29]([C:26]2[CH:25]=[CH:24][C:23]([C:9]3[CH:10]=[CH:11][CH:12]=[C:13]([N:15]4[CH2:16][CH2:17][O:18][CH2:19][CH2:20]4)[N:14]=3)=[CH:28][CH:27]=2)[CH3:30])[CH2:36][CH2:35]1

Participants

3

Reactant 2

HCID 44599033(S)-3-((S)-1-(4-bromophenyl)ethyl)-6-(2-hydroxy-2-methylpropyl)-6-phenyl-1,3-oxazinan-2-oneHCID 457863324-[6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]morpholine

Product 1

HCID 70652442HCID 70652442, compound

Procedure

The title compound was prepared from 4-[6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl]morpholine (purchased from CombiPhos Catalysts Inc., Princeton, N.J., USA) and (S)-3-[(S)-1-(4-bromophenyl)ethyl]-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-1,3-oxazinan-2-one following a procedure analogous to that described in Example 35. LC (method 5): tR=1.68 min; Mass spectrum (ESI+): m/z=516 [M+H]+; 1H NMR (CD3OD) δ 0.95 (s, 3H), 1.24 (s, 3H), 1.58 (d, 3H), 2.17 (s, 2H), 2.25 (m, 1H), 2.47 (m, 2H), 3.08 (m, 1H), 3.66 (m, 4H), 3.83 (m, 4H), 5.58 (q, 1H), 7.12 (4H), 7.25-7.40 (5H), 7.63 (d, 2H), 7.88 (m, 1H).

Sources & evidence

ORD record
ord-75dfa60a28504f69b159a7ddb5c6033e
Source dataset
uspto-grants-2015_01
Patent number
US08933072B2

Reaction notes

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