Benzyl(methoxymethyl)((trimethylsilyl)methyl)amine → 3-(trans-1-benzyl-4-methyl-3-pyrrolidinylcarbonyl)-4-(S)-isopropyl-2-oxazolidinone

HRID 53344

Reaction equation

HRID 53344 reaction equation
[CH3:1]/[CH:2]=[CH:3]/[C:4]([N:6]1[C@@H:10]([CH:11]([CH3:13])[CH3:12])[CH2:9][O:8][C:7]1=[O:14])=[O:5].[CH2:15]([N:22]([CH2:26][Si](C)(C)C)[CH2:23]OC)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>>[CH2:15]([N:22]1[CH2:23][C@@H:2]([CH3:1])[C@H:3]([C:4]([N:6]2[C@@H:10]([CH:11]([CH3:13])[CH3:12])[CH2:9][O:8][C:7]2=[O:14])=[O:5])[CH2:26]1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 5702601(4S)-3-[(E)-but-2-enoyl]-4-propan-2-yl-1,3-oxazolidin-2-one

Product 1

HCID 228718333-(trans-1-benzyl-4-methyl-3-pyrrolidinylcarbonyl)-4-(S)-isopropyl-2-oxazolidinoneYield 90.8%

Procedure

3-(trans-3-Methyl-2-propenoyl)-4-(S)-isopropyl-2-oxazolidinone (197 mg, 1.00 mmol, Aldrich) was reacted with N-benzyl-N-(methoxymethyl)trimethylsilylmethylamine (238 mg, 1.00 mmol) according to the procedure of Example 1d, to afford the title compound (300 mg). The diasteromers were separated as in Example 1d, and the (3R,4R)-isomer was taken to the next step. MS m/z 331 (M+H)+. The (3S,4S)-isomer was taken to Example 4. MS m/z 331 (M+H)+.

Sources & evidence

ORD record
ord-e6aa37d8e9db4fa8a4e1e47ea5c297b5
Source dataset
uspto-grants-1997_04
Patent number
US05618949

Linked notes

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