1-Benzyl 3-(4-methoxyphenyl)methyl (3RS,4SR)-3-[2-(tert-butoxy)-2-oxoethyl]-4-methylpyrrolidine-1,3-dicarboxylate → 1-benzyl 3-(4-methoxyphenyl)methyl (3R*,4S*)-3-[2-(tert-butoxy)-2-oxoethyl]-4-methylpyrrolidine-1,3-dicarboxylate

HRID 446003Notes

Reaction equation

HRID 446003 reaction equation
[C:1]([O:5][C:6](=[O:36])[CH2:7][C:8]1([C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)=[O:25])[CH:12]([CH3:13])[CH2:11][N:10]([C:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:15])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2]>CCCCCC.C(O)C>[C:1]([O:5][C:6](=[O:36])[CH2:7][C@@:8]1([C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)=[O:25])[C@H:12]([CH3:13])[CH2:11][N:10]([C:14]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:15])[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

3

Reactant 1

HCID 780519391-Benzyl 3-(4-methoxyphenyl)methyl (3RS,4SR)-3-[2-(tert-butoxy)-2-oxoethyl]-4-methylpyrrolidine-1,3-dicarboxylate

Product 1

HCID 712936671-benzyl 3-(4-methoxyphenyl)methyl (3R*,4S*)-3-[2-(tert-butoxy)-2-oxoethyl]-4-methylpyrrolidine-1,3-dicarboxylateYield 40.5%

Reagents, catalysts & solvents 1

HCID 21879635Ethanol hexaneSolvent

Procedure

1-Benzyl 3-(4-methoxyphenyl)methyl (3RS,4SR)-3-[2-(tert-butoxy)-2-oxoethyl]-4-methylpyrrolidine-1,3-dicarboxylate obtained in Example 2h (7.2 g, 14.5 mmol) was optically resolved repeatedly by HPLC(CHIRALPAK AD-H (2 cm diameter×25 cm), elution solvent: hexane/ethanol=85/15, flow rate: 8-10 ml/min.) to give a chiral form corresponding to the peak with a shorter retention time (2.92 g, yield: 40.5%).

Sources & evidence

ORD record
ord-c958386e40de43b6ad2ceee3ab3afb1f
Source dataset
uspto-grants-2013_07
Patent number
US08476301B2

Reaction notes

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