Trimethylsilyldiazomethane → (2R,4R)-4-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

HRID 2185414Notes

Reaction equation

HRID 2185414 reaction equation
[OH:1][C@H:2]1[CH2:6][N:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C@@H:4]([C:14]([OH:16])=[O:15])[CH2:3]1.[CH3:17][Si](C=[N+]=[N-])(C)C>CCCCCC>[CH3:17][O:15][C:14](=[O:16])[C@H:4]1[CH2:3][C@@H:2]([OH:1])[CH2:6][N:5]1[C:7]([O:9][C:10]([CH3:11])([CH3:12])[CH3:13])=[O:8]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 688616N-Boc-cis-4-hydroxy-D-proline

Product 1

HCID 6951202(2R,4R)-4-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent2×

Procedure

A solution of 2 M (triimethylsilyl)diazomethane in hexane (4 mL) was added to a solution of cis-4-hydroxy-N-tert-butoxycarbonyl-D-proline (916 mg) at 0° C. After stirring at room temperature for 1 hr, a solution of 2 M (trimethylsilyl)diazomethane in hexane (6 mL) was added additionally and stirred at room temperature for 30 min. The solvents were evaporated in vacuo to afford the title compound (971 mg) as a pale yellow oil.

Workup

  1. stirringstirred at room temperature for 30 min
  2. customThe solvents were evaporated in vacuo

Sources & evidence

ORD record
ord-bf3013af767d4dc2af9a33f8ef2c3310
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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