Tert-butyl acetoacetate → (2S,4R)-4-cyclopropylmethanesulfonyl-1-(3-oxo-butyryl)-pyrrolidine-2-carboxylic Acid Methyl Ester

HRID 1697714Notes

Reaction equation

HRID 1697714 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10]([C@@H:12]1[CH2:16][C@@H:15]([S:17]([CH2:20][CH:21]2[CH2:23][CH2:22]2)(=[O:19])=[O:18])[CH2:14][NH:13]1)=[O:11].[C:24](OC(C)(C)C)(=[O:29])[CH2:25][C:26]([CH3:28])=[O:27]>C(N(CC)CC)C>[CH3:8][O:9][C:10]([C@@H:12]1[CH2:16][C@@H:15]([S:17]([CH2:20][CH:21]2[CH2:23][CH2:22]2)(=[O:18])=[O:19])[CH2:14][N:13]1[C:24](=[O:29])[CH2:25][C:26](=[O:27])[CH3:28])=[O:11]

Participants

4

Reactant 2

HCID 15538Tert-butyl acetoacetateHCID 66770846(2S,4R)-4-Cyclopropylmethanesulfonyl-pyrrolidine-2-carboxylic Acid Methyl Ester Trifluoroacetate

Product 1

HCID 86646863(2S,4R)-4-cyclopropylmethanesulfonyl-1-(3-oxo-butyryl)-pyrrolidine-2-carboxylic Acid Methyl Ester

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

In analogy to the procedure described in example 192f, (2S,4R)-4-cyclopropylmethanesulfonyl-pyrrolidine-2-carboxylic acid methyl ester trifluoroacetate was reacted with tert-butyl acetoacetate in the presence of triethylamine to give the title compound as brown solid. MS (ESI): m/z=332.2 [M+H]+.

Sources & evidence

ORD record
ord-63e4c8bff5e94068818d4e6a9d29518c
Source dataset
uspto-grants-2012_04
Patent number
US08163793B2

Reaction notes

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