HCID 66939725, compound → HCID 66939726, compound

HRID 1442969Notes

Reaction equation

HRID 1442969 reaction equation
[CH:1]([CH:4]1[CH2:9][CH2:8][CH:7]([CH3:10])[CH2:6][CH:5]1[O:11][C:12]([CH:14]1[CH2:18][C:17](=[CH:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=2)[CH2:16][N:15]1[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[O:13])([CH3:3])[CH3:2]>C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH:1]([CH:4]1[CH2:9][CH2:8][CH:7]([CH3:10])[CH2:6][CH:5]1[O:11][C:12]([CH:14]1[CH2:18][CH:17]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([F:26])[CH:21]=2)[CH2:16][N:15]1[C:27]([O:29][C:30]([CH3:33])([CH3:31])[CH3:32])=[O:28])=[O:13])([CH3:3])[CH3:2]

Participants

3

Reactant 1

HCID 66939725HCID 66939725, compound

Product 1

HCID 66939726HCID 66939726, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 21584019Toluene ethylacetateSolvent

Procedure

4-(3-Fluoro-benzylidene)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-(2-isopropyl-5-methyl-cyclohexyl)ester (1.20 g, 2.61 mmol) was dissolved in ethyl acetate:toluene (1:1, 12 ml). The solution was submitted to hydrogenation on platinum oxide (120 mg, 10% by weight) at 25° C. and 15 psi for 1 hour. The reaction mixture was filtered through arbocel and the filtrate reduced under pressure. The residue was purified by flashmaster chromatography eluting with heptane:ethyl actetate (15:1) to yield the title compound as a colourless oil (1.11 g, 91%).

Workup

  1. customwas submitted to hydrogenation on platinum oxide (120 mg, 10% by weight) at 25° C.
  2. filtrationThe reaction mixture was filtered through arbocel
  3. customThe residue was purified by flashmaster chromatography
  4. washeluting with heptane

Sources & evidence

ORD record
ord-666de4a8c2b3488686aa946ffe3fe362
Source dataset
uspto-grants-2010_02
Patent number
US07659305B2

Reaction notes

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