3-Carboxyphenylboronic acid → 3-(1-(Tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)benzoic acid

HRID 643571Notes

Reaction equation

HRID 643571 reaction equation
B(O)(O)C1C=CC=C(C(O)=O)C=1.FC(F)(F)S(OC1CCN(C(OC(C)(C)C)=O)CC=1)(=O)=O.C([O:36][C:37]([C:39]1[CH:40]=[C:41]([C:45]2[CH2:46][CH2:47][N:48]([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[CH2:49][CH:50]=2)[CH:42]=[CH:43][CH:44]=1)=[O:38])C>>[C:54]([O:53][C:51]([N:48]1[CH2:47][CH:46]=[C:45]([C:41]2[CH:40]=[C:39]([CH:44]=[CH:43][CH:42]=2)[C:37]([OH:38])=[O:36])[CH2:50][CH2:49]1)=[O:52])([CH3:57])([CH3:55])[CH3:56]

Participants

4

Reactant 3

HCID 27339573-Carboxyphenylboronic acidHCID 10991161Tert-butyl 4-(trifluoromethanesulfonyloxy)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 57880536tert-butyl 4-[3-(ethoxycarbonyl)phenyl]-3,6-dihydropyridine-1(2H)-carboxylate2×

Product 1

HCID 592610253-(1-(Tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl)benzoic acid

Procedure

3-(dihydroxyborane)benzoic acid (4.65 g, 28.0 mmol) was coupled to tert-butyl 4-{[(trifluoromethyl)sulfonyl]oxy}-3,6-dihydropyridine-1(2H)-carboxylate (6.65 g, 20.0 mmol) in an analogous fashion to that described previously for the synthesis of tert-butyl 4-[3-(ethoxycarbonyl)phenyl]-3,6-dihydropyridine-1(2H)-carboxylate (INTERMEDIATE 6, Step A) to give 3-[1-(tert-butoxycarbonyl)-1,2,3,6-tetrahydropyridin-4-yl]benzoic acid.

Sources & evidence

ORD record
ord-90d0d8e5a9a44a4c9303a48a4eddbb3e
Source dataset
uspto-grants-2010_04
Patent number
US07700591B2

Reaction notes

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