HCID 86621621, compound → HCID 68438656, compound

HRID 2246954Notes

Reaction equation

HRID 2246954 reaction equation
CON(C)[C:4](=[O:47])[CH2:5][CH:6]1[CH2:11][CH:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[CH:9]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]3[O:30][CH2:29][CH2:28][N:27]([CH2:31][CH2:32][CH2:33][O:34][CH3:35])[C:26]=3[CH:36]=2)[CH2:8][N:7]1[S:37]([C:40]1[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=1)(=[O:39])=[O:38].[CH2:49]([Mg]Br)[CH3:50]>>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([C@@H:10]2[C@@H:9]([O:20][CH2:21][C:22]3[CH:23]=[CH:24][C:25]4[O:30][CH2:29][CH2:28][N:27]([CH2:31][CH2:32][CH2:33][O:34][CH3:35])[C:26]=4[CH:36]=3)[CH2:8][N:7]([S:37]([C:40]3[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=3)(=[O:39])=[O:38])[C@@H:6]([CH2:5][C:4](=[O:47])[CH2:49][CH3:50])[CH2:11]2)=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 86621621HCID 86621621, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 68438656HCID 68438656, compound

Procedure

Similar to example 29b by, 1.0 g of N-methoxy-2-[4-(4-methoxy-phenyl)-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulfonyl)-piperidin-2-yl]-N-methyl-acetamide (from example 29c) in the presence of ethyl magnesium bromide are used to afford the title compound after flash chromatography (SiO2 60 F) as a colourless oil. Rf=0.20 (EtOAc-heptane 1:1); Rt=5.13.

Sources & evidence

ORD record
ord-03ace3bf9b264c5a8896535da3521cfe
Source dataset
uspto-grants-2010_03
Patent number
US07687495B2

Reaction notes

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