Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate → HCID 23571082, compound

HRID 1823972Notes

Reaction equation

HRID 1823972 reaction equation
Br[C:2]1[S:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]3[CH2:17][C@H:16]4[C@:18]5([CH2:22][N:21]([CH2:23][C:24]([F:27])([F:26])[F:25])[S:20](=[O:29])(=[O:28])[NH:19]5)[C@H:13]([CH2:14][CH2:15]4)[CH2:12][C:11]=3[CH:30]=2)=[N:4][CH:3]=1.CC1(C)C(C)(C)OB(C2C=CC3C[C@H]4[C@]5(CN(CC(F)(F)F)S(=O)(=O)N5)[C@H](CC4)CC=3C=2)O1.[C:64]([O:68][C:69]([N:71]1[CH2:76][CH:75]=[C:74](B2OC(C)(C)C(C)(C)O2)[CH2:73][CH2:72]1)=[O:70])([CH3:67])([CH3:66])[CH3:65]>CS(C)=O>[C:64]([O:68][C:69]([N:71]1[CH2:72][CH:73]=[C:74]([C:2]2[S:6][C:5]([C:7]3[CH:8]=[CH:9][C:10]4[CH2:17][C@H:16]5[C@:18]6([CH2:22][N:21]([CH2:23][C:24]([F:27])([F:26])[F:25])[S:20](=[O:29])(=[O:28])[NH:19]6)[C@H:13]([CH2:14][CH2:15]5)[CH2:12][C:11]=4[CH:30]=3)=[N:4][CH:3]=2)[CH2:75][CH2:76]1)=[O:70])([CH3:67])([CH3:65])[CH3:66]

Participants

5

Reactant 3

HCID 4642098Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 23571079[6s,9r,11r]2',3',4',5,5',6,7,8,9,10-Decahydro-2-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-5'-(2,2,2-trifluoroethyl)spiro[6,9-methanobenzocyclooctene-11,3'-[1,2,5]thiadiazole]1',1'-dioxideHCID 23571107HCID 23571107, compound

Product 1

HCID 23571082HCID 23571082, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Prepared using [6S,9R,11R]2′,3′,4′,5,5′,6,7,8,9,10-Decahydro-2-(5-bromothiazol-2-yl)-5′-(2,2,2-trifluoroethyl)-spiro[6,9-methanobenzocyclooctene-11,3′-[1,2,5]thiadiazole]1′,1′-dioxide (prepared using the homochiral boronate from Example 24 Step 1 by the method described for Example 36 Steps 1–2) and the boronate from Example 39 Step 2 using the method described for Example 36 Step 3. MS (ES+) 625 ([MH]+); [α]D=−11 (c=0.62, DMSO, 23° C.).

Workup

  1. customPrepared
  2. customprepared

Sources & evidence

ORD record
ord-6504c547d31748d283795cfae11a8f9b
Source dataset
uspto-grants-2006_05
Patent number
US07041689B2

Reaction notes

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