Acetic Anhydride → HCID 57016811, compound

HRID 1282262Notes

Reaction equation

HRID 1282262 reaction equation
[C:1]([O:5][C:6]([C@@H:8]1[N:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C@H:11]([CH:20]=[CH2:21])[C@H:10]([CH2:22][OH:23])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:24](OC(=O)C)(=[O:26])[CH3:25]>CN(C)C1C=CN=CC=1.N1C=CC=CC=1>[C:1]([O:5][C:6]([C@@H:8]1[N:12]([CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C@H:11]([CH:20]=[CH2:21])[C@H:10]([CH2:22][O:23][C:24](=[O:26])[CH3:25])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 57231265HCID 57231265, compound

Product 1

HCID 57016811HCID 57016811, compoundYield 81.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

(±)-(2R,3R,5R)-1-Benzyl-2-vinyl-3-(hydroxymethyl)-pyrrolidine-5-carboxylic acid t-butyl ester (54.2 g, 0.17 mol) and 4-(dimethylamino)pyridine (0.5 g, 4.1 mmol), in anhydrous pyridine (400 mL) was reacted with acetic anhydride (30 mL, 0.32 mol) at 0° C. for 1 hour then allowed to warm to room temperature. The reaction was stirred an additional 16 hours. The pyridine was removed in vacuo at 30° C. The residue was partitioned between ethyl acetate (100 mL) and of water (400 mL). The aqueous layer was extracted with ethyl acetate (3×100 mL) and the combined ethyl acetate layers were washed with brine, dried with MgSO4, filtered, and concentrated. The crude product was purified by chromatography on silica gel using 10% ethyl acetate/hexanes to provide the title compound as a colorless oil (yield: 49.6 g, 81%).

Workup

  1. customThe pyridine was removed in vacuo at 30° C
  2. customThe residue was partitioned between ethyl acetate (100 mL) and of water (400 mL)
  3. extractionThe aqueous layer was extracted with ethyl acetate (3×100 mL)
  4. washthe combined ethyl acetate layers were washed with brine
  5. dry with materialdried with MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product was purified by chromatography on silica gel using 10% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-3ce82aaece61413c8898ec267a313f1d
Source dataset
uspto-grants-2002_09
Patent number
US06455571B1

Reaction notes

Loading…