Acetic Anhydride → Tert-butyl 3-acetamido-4-hydroxypyrrolidine-1-carboxylate

HRID 2353441Notes

Reaction equation

HRID 2353441 reaction equation
[NH2:1][C@H:2]1[C@H:6]([OH:7])[CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.[C:15](OC(=O)C)(=[O:17])[CH3:16]>ClCCl>[C:15]([NH:1][CH:2]1[CH:6]([OH:7])[CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1)(=[O:17])[CH3:16]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 11275699(3R,4R)-3-Amino-1-Boc-4-hydroxypyrrolidine

Product 1

HCID 68711974Tert-butyl 3-acetamido-4-hydroxypyrrolidine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of tert-butyl trans-3-amino-4-hydroxypyrrolidine-1-carboxylate (500 mg, the compound of Step A, Intermediate 15), in dichloromethane (20 mL) at 0° C. was added acetic anhydride (0.24 mL) and stirring continued for 1 h. The reaction mixture was quenched with saturated sodium bicarbonate (40 mL), extracted with dichlomethane (4×20 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and evaporated to yield the title compound which was used in the next step without further purification.

Workup

  1. customThe reaction mixture was quenched with saturated sodium bicarbonate (40 mL)
  2. extractionextracted with dichlomethane (4×20 mL)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-928753ba6bc34d9f95ccd96d217d0dc2
Source dataset
uspto-grants-2010_07
Patent number
US07750034B2

Reaction notes

Loading…