Phthalimide → HCID 67394528, compound

HRID 1403690Notes

Reaction equation

HRID 1403690 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([N:14]3[CH2:19][CH2:18][CH:17]([CH2:20][CH2:21]O)[CH2:16][CH2:15]3)[CH:11]=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:42]1(=[O:52])[NH:46][C:45](=[O:47])[C:44]2=[CH:48][CH:49]=[CH:50][CH:51]=[C:43]12.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C(OCC)(=O)C.C1CCCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:13]=[C:12]([N:14]3[CH2:15][CH2:16][CH:17]([CH2:20][CH2:21][N:46]4[C:42](=[O:52])[C:43]5[C:44](=[CH:48][CH:49]=[CH:50][CH:51]=5)[C:45]4=[O:47])[CH2:18][CH2:19]3)[CH:11]=[CH:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 67130432HCID 67130432, compound

Product 1

HCID 67394528HCID 67394528, compoundYield 48.9%

Reagents, catalysts & solvents 2

HCID 8078CyclohexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The procedure described in Example 1 (step 1.2.) is followed, Starting from g (6.66 mmol) of 2-[6′-(4-fluorophenyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-yl]ethanol, prepared in step 4.1., 2.096 g (7.99 mmol) of triphenylphosphine, 1.077 g (7.32 mmol) of phthalimide and 1.61 g (7.99 mmol) of diisopropyl azodicarboxylate (DIAD), and after chromatography on silica gel, eluting with a 15/85 mixture of ethyl acetate and cyclohexane, gives 1.4 g of pure product in the form of a white powder.

Workup

  1. customprepared in step 4.1

Sources & evidence

ORD record
ord-5887009769d34b9db3af8825f1edca0c
Source dataset
uspto-grants-2014_12
Patent number
US08912218B2

Reaction notes

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