HCID 178418361, compound → HCID 178455342, compound

HRID 415983Notes

Reaction equation

HRID 415983 reaction equation
C([O:8][C:9]1[CH:35]=[C:34]([Cl:36])[C:12]([CH2:13][CH:14]2[CH2:18][CH2:17][N:16]([C@H:19]3[CH2:24][CH2:23][C@@H:22]([O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27])[CH2:21][CH2:20]3)[C:15]2=[O:33])=[C:11]([Cl:37])[CH:10]=1)C1C=CC=CC=1.[H][H]>O1CCCC1.[OH-].[OH-].[Pd+2]>[C:29]([Si:26]([CH3:28])([CH3:27])[O:25][C@@H:22]1[CH2:23][CH2:24][C@H:19]([N:16]2[CH2:17][CH2:18][CH:14]([CH2:13][C:12]3[C:11]([Cl:37])=[CH:10][C:9]([OH:8])=[CH:35][C:34]=3[Cl:36])[C:15]2=[O:33])[CH2:20][CH2:21]1)([CH3:31])([CH3:30])[CH3:32]

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178455343HCID 178455343, compound

Product 1

HCID 178455342HCID 178455342, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Add a solution of 3-(4-benzyloxy-2,6-dichloro-benzyl)-cis-1-[4-(tert-butyl-dimethyl-silanyloxy)-cyclohexyl]-pyrrolidin-2-one (8.5 g 15.1 mmol) in 25 mL tetrahydrofuran to 0.5 g Pearlman's catalyst and hydrogenate the resulting mixture under a balloon of hydrogen gas 2 hr. Filter through Celite® and concentrate to get a solid. Purify by silica gel chromatography using hexanes/ethyl acetate to recover 4.4 g (61%) of product.

Workup

  1. filtrationFilter through Celite®
  2. concentrationconcentrate
  3. customto get a solid
  4. customPurify by silica gel chromatography
  5. customto recover 4.4 g (61%) of product

Sources & evidence

ORD record
ord-23801aacfea14bb7b8de0c7da7a32790
Source dataset
uspto-grants-2012_01
Patent number
US08088776B2

Reaction notes

Loading…