Diethyl Ether → (2S,4S)-1-Benzyl 2-methyl 4-methoxypyrrolidine-1,2-dicarboxylate

HRID 1961381Notes

Reaction equation

HRID 1961381 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][C@@H:14]([O:16][CH3:17])[CH2:13][C@H:12]1[C:18]([OH:20])=[O:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:21](OCC)C.C[Si](C=[N+]=[N-])(C)C>CO>[CH3:17][O:16][C@@H:14]1[CH2:15][N:11]([C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[O:10])[C@H:12]([C:18]([O:20][CH3:21])=[O:19])[CH2:13]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 167693TrimethylsilyldiazomethaneHCID 12849520(2S,4S)-1-[(Benzyloxy)carbonyl]-4-methoxypyrrolidine-2-carboxylic acid

Product 1

HCID 14036172(2S,4S)-1-Benzyl 2-methyl 4-methoxypyrrolidine-1,2-dicarboxylateYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (2S,4S)-1-(benzyloxycarbonyl)-4-methoxypyrrolidine-2-carboxylic acid (3.0 g, 0.01 mol) in methanol (40 mL0 and diethyl ether (20 mL) was added (trimethylsilyl)diazomethane (2.0 M solution in diethyl ether, 6.4 mL, 0.013 mol) dropwise under ice-bath. The reaction mixture was stirred at room temperature for 1 h. Concentration of the reaction mixture gave (2S,4S)-1-benzyl 2-methyl 4-methoxypyrrolidine-1,2-dicarboxylate 18B (3.2 g, 100%) as an oil which was used in the next step without purification. 1H NMR (CDCl3, 400 MHz) δ 7.27-7.36 (m, 5H), 5.04-5.19 (m, 2H), 4.39-4.50 (m, 1H), 3.91-3.94 (m, 1H), 3.53-3.72 (m, 5H), 3.24 (s, 3H), 2.21-2.35 (m, 2H).

Sources & evidence

ORD record
ord-259ad48bcc5449fcabdc0afd4eaabb81
Source dataset
uspto-grants-2013_04
Patent number
US08415340B2

Reaction notes

Loading…