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

반응식

[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

참가 물질

반응물 2

HCID 8028Tetrahydrofuran

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

생성물 1

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

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록: ord-9b0a2c977b72425c90a00e57ab227d60
출처 데이터셋: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
특허 번호: US07094783B2

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