Trimethylsilyldiazomethane → (2S,4S)-1-Benzyl 2-methyl 4-(2,2-difluoroethoxy)pyrrolidine-1,2-dicarboxylate

HRID 1961417Notes

Reaction equation

HRID 1961417 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@@H:14]([O:16][CH2:17][CH:18]([F:20])[F:19])[CH2:13][C@H:12]1[C:21]([OH:23])=[O:22])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Si](C=[N+]=[N-])(C)(C)[CH3:25]>CO.CCOCC>[F:19][CH:18]([F:20])[CH2:17][O:16][C@@H:14]1[CH2:15][N:11]([C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[O:10])[C@H:12]([C:21]([O:23][CH3:25])=[O:22])[CH2:13]1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 59436454(2S,4S)-1-(Benzyloxycarbonyl)-4-(2,2-difluoroethoxy)pyrrolidine-2-carboxylic acid

Product 1

HCID 59436413(2S,4S)-1-Benzyl 2-methyl 4-(2,2-difluoroethoxy)pyrrolidine-1,2-dicarboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of (2S,4S)-1-(benzyloxycarbonyl)-4-(2,2-difluoroethoxy)pyrrolidine-2-carboxylic acid (2.0 g, 6.07 mmol) in MeOH and ether (80 ml) (1:1) was added TMS-diazomethane (4.56 mL, 9.11 mmol) (2.0M solution in ether) dropwise at 0° C. The reaction mixture was stirred at RT for 1 h and concentrated. The residue was used in the next step.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-0b113bc95ef64ea8b0cf18428500eeac
Source dataset
uspto-grants-2013_04
Patent number
US08415340B2

Reaction notes

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