Tetrahydrofuran → tert-Butyl (S)-5-(methylsulfanyl)-3,4-dihydro-2H-pyrrole-2-carboxylate

反応式

[S:1]=[C:2]1[NH:6][C@H:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH2:4][CH2:3]1.[CH2:14]1COCC1>>[CH3:14][S:1][C:2]1[CH2:3][CH2:4][C@@H:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[N:6]=1

参加物

反応物 2

HCID 8028Tetrahydrofuran

HCID 14416882tert-Butyl (S)-5-thioxo-2-pyrrolidinecarboxylate

生成物 1

HCID 53965507tert-Butyl (S)-5-(methylsulfanyl)-3,4-dihydro-2H-pyrrole-2-carboxylate収率 91%

実験手順

To a solution of thiolactam 1b (10.50 g, 52.2 mmol) in 200 mL THF at rt, was added Mel (13.0 mL, 208.7 mmol). The mixture was stirred for 3.5 h, then concentrated. The residue was partitioned between CH2Cl2 and sat. NaHCO3 and the aqueous phase was extracted with CH2Cl2 (3×). The combined organic extract was dried (Na2SO4) and concentrated to afford 10.17 g (91%) of the title compound, 1c, as a brown oil. 1H NMR (300 MHz, CDCl3) δ 4.60 (dd, J=6.2, 7.3, 1H), 2.83–2.58 (m, 2H), 2.49 (s, 3H), 2.37–2.22 (m, 1H), 2.17–2.03 (m, 1H), 1.48 (s, 9H).

後処理

concentrationconcentrated
customThe residue was partitioned between CH2Cl2 and sat. NaHCO3
extractionthe aqueous phase was extracted with CH2Cl2 (3×)
extractionThe combined organic extract
dry with materialwas dried (Na2SO4)
concentrationconcentrated

出典と根拠

ORDレコード: ord-9b0a2c977b72425c90a00e57ab227d60
出典データセット: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US07094783B2

反応ノート

読み込み中…

参加物