2-Bromomethylnaphthalene → HCID 86604513, compound

HRID 1005220Notes

Reaction equation

HRID 1005220 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][N:16]([CH:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:21][CH:20]2[OH:32])[C:15](=[O:33])[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:34]([O:41][CH2:42][CH2:43][CH2:44][O:45][C:46]1[CH:51]=[CH:50][N:49]([CH:52]2[CH:57]([OH:58])[CH2:56][CH2:55][N:54]([C:59]([O:61][C:62]([CH3:65])([CH3:64])[CH3:63])=[O:60])[CH2:53]2)[C:48](=[O:66])[CH:47]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.Br[CH2:68][C:69]1[CH:78]=[CH:77][C:76]2[C:71](=[CH:72][CH:73]=[CH:74][CH:75]=2)[CH:70]=1>>[CH2:34]([O:41][CH2:42][CH2:43][CH2:44][O:45][C:46]1[CH:51]=[CH:50][N:49]([CH:52]2[CH:57]([O:58][CH2:68][C:69]3[CH:78]=[CH:77][C:76]4[C:71](=[CH:72][CH:73]=[CH:74][CH:75]=4)[CH:70]=3)[CH2:56][CH2:55][N:54]([C:59]([O:61][C:62]([CH3:63])([CH3:65])[CH3:64])=[O:60])[CH2:53]2)[C:48](=[O:66])[CH:47]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:18]=[CH:17][N:16]([CH:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28]([CH3:30])([CH3:29])[CH3:31])=[O:26])[CH2:21][CH:20]2[O:32][CH2:68][C:69]2[CH:78]=[CH:77][C:76]3[C:71](=[CH:72][CH:73]=[CH:74][CH:75]=3)[CH:70]=2)[C:15](=[O:33])[CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 703202-BromomethylnaphthaleneHCID 86604515HCID 86604515, compoundHCID 86604516HCID 86604516, compound

Product 2

HCID 86604513HCID 86604513, compoundHCID 86604514HCID 86604514, compound

Procedure

In an analogous manner to that described in Example 145 (h), from a mixture of tert-butyl (3'RS,4'RS)-4-(3-benzyloxy-propoxy)-3'-hydroxy-2-oxo-3',4',5',6'-tetrahydro-2H,2'H-[1,4']bipyridine-1'-carboxylate and tert-butyl (3'RS,4'RS)-4-(3-benzyloxy-propoxy)-4'-hydroxy-2-oxo-3',4',5',6'-tetrahydro-2H,2'H-[1,3']bipyridine-1'-carboxylate by means of alkylation with 2-bromomethyl-naphthalene and after chromatographic separation of the two isomers on silica gel using a 1:4 mixture of methylene chloride and ethyl acetate as the eluent there was obtained tert-butyl (3'RS,4'RS)-4-(3-benzyloxy-propoxy)-4'-(naphthalen-2-ylmethoxy)-2-oxo-3',4',5',6'-tetrahydro-2H,2'H-[1,3']bipyridine-1'-carboxylate, (Rf : 0.64, SiO2 ; methylene chloride:ethyl acetate=1:4 v/v), and tert-butyl (3'RS,4'RS)-4-(3-benzyloxy-propoxy)-3'-(naphthalen-2-ylmethoxy)-2-oxo-3',4',5',6'-tetrahydro-2H,2'H-[1,4']bipyridine-1'-carboxylate, MS: 599 (M+H)+, (Rf : 0.44, SiO2 ; methylene chloride:ethyl acetate=1:4 v/v), each as a yellowish oil.

Workup

  1. customafter chromatographic separation of the two isomers on silica gel using
  2. additiona 1:4 mixture of methylene chloride and ethyl acetate as the eluent there

Sources & evidence

ORD record
ord-129095f1ffa449978b8a7bbf36dac73a
Source dataset
uspto-grants-2000_04
Patent number
US06051712

Reaction notes

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