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

HRID 53346

反応式

HRID 53346 の反応式
[CH3:1]/[CH:2]=[CH:3]/[C:4]([N:6]1[C@H:10]([CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:9][O:8][C:7]1=[O:18])=[O:5].[CH2:19]([N:26]([CH2:30][Si](C)(C)C)[CH2:27]OC)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>>[CH2:19]([N:26]1[CH2:27][C@@H:2]([CH3:1])[C@H:3]([C:4]([N:6]2[C@H:10]([CH2:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:9][O:8][C:7]2=[O:18])=[O:5])[CH2:30]1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

参加物

3

反応物 2

HCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 11481966(4R)-3-((E)-2-butenoyl)-4-(phenylmethyl)-2-oxazolidinone

生成物 1

HCID 228718293-(trans-1-benzyl-4-methyl-3-pyrrolidinylcarbonyl)-4-(R)-benzyl-2-oxazolidinone収率 44.9%

実験手順

The compound from step 5a (245 mg, 1.00 mmol) was reacted with N-benzyl-N-(methoxymethyl)trimethylsilylmethylamine (254 mg, 1.2 mmol) according to the procedure of Example 1d, to afford the title compound (170 mg). MS m/z 379 (M+H)+. NMR (CDCl3) d 7.15-7.40 (10H, m), 4.69 (1H, m), 4.20 (1H, dd, J=16.5, 9.0 Hz), 4.18 (1H, dd, J=9.0, 6.0 Hz), 3.71 (1H, d, J=13.5 Hz), 3.65 (1H, m), 3.56 (1H, d, J+13.5 Hz), 3.24 (1H, dd, J=13.5, 3.3 Hz), 2.70-3.10 (4H, m), 2.17 (1H, dd, 8.4, 7.5 Hz), 1.08 (3H, d, J=6.9 Hz).

出典と根拠

ORDレコード
ord-ce99d4a1001c4ac0a6ddb0990ed2ba11
出典データセット
uspto-grants-1997_04
特許番号
US05618949

関連ノート

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