HCID 69427734, compound → HCID 69427724, compound

HRID 458369Notes

Reaction equation

HRID 458369 reaction equation
[C:1]([O:5][C@H:6]1[CH2:10][N:9]([S:11]([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)(=[O:13])=[O:12])[C@H:8]([CH2:24][O:25][CH2:26]/[CH:27]=[CH:28]/[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:7]1)([CH3:4])([CH3:3])[CH3:2]>C(O)C.O1CCOCC1.[Pd]>[C:1]([O:5][C@H:6]1[CH2:10][N:9]([S:11]([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)(=[O:13])=[O:12])[C@H:8]([CH2:24][O:25][CH2:26][CH2:27][CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH2:7]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 69427734HCID 69427734, compound

Product 1

HCID 69427724HCID 69427724, compoundYield 93.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 22560076Dioxan ethanolSolvent

Procedure

Hydrogenation: A solution of (E)-(2S,4R)-4-tert-butoxy-1-(naphthalene-2-sulfonyl)-2-(3-phenyl-allyloxymethyl)-pyrrolidine (2.3 g) in ethanol/dioxane 1:2 (75 ml) was hydrogenated in the presence of 10% palladium on charcoal (0.50 g) at 1.1 bar and room temperature for 4 h. The reaction mixture was filtered over a pad of celite and washed with ethanol. The filtrate was concentrated, and the residue was chromatographed on silica gel using EtOAc/hexane 1:4 as eluent to obtain (2S,4R)-4-tert-butoxy-1-(naphthalene-2-sulfonyl)-2-(3-phenyl-propoxymethyl)-pyrrolidine (2.16 g) as a gum, MS: 482 (MH+).

Workup

  1. filtrationThe reaction mixture was filtered over a pad of celite
  2. washwashed with ethanol
  3. concentrationThe filtrate was concentrated
  4. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-523e162de10a4fa99dd949f4313316c8
Source dataset
uspto-grants-2007_03
Patent number
US07189756B2

Reaction notes

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