Acetone → Tert-butyl 4-(iodomethyl)piperidine-1-carboxylate

HRID 1386772노트

반응식

HRID 1386772 반응식
CS(O[CH:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1)(=O)=O.[I-:19].[Na+].[CH3:21]C(C)=O>>[C:15]([O:14][C:12]([N:9]1[CH2:10][CH2:11][CH:6]([CH2:21][I:19])[CH2:7][CH2:8]1)=[O:13])([CH3:18])([CH3:17])[CH3:16]

참가 물질

4

반응물 3

HCID 180AcetoneHCID 5238Sodium IodideHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

생성물 1

HCID 10448961Tert-butyl 4-(iodomethyl)piperidine-1-carboxylate

실험 절차

A mixture of 1-(t-butoxycarbonyl)piperidin-4-yl methanesulfonate (13.58 g, 46.4 mmol) and sodium iodide (34.68 g, 232 mmol) in acetone (80 mL) was heated to reflux for 3 h. The mixture was partitioned between ether (350 mL) and H2O (350 mL). The organic layer was washed with saturated aq. NaCl (250 mL), and the aqueous layers were extracted in succession with ether (250 mL). The combined organic layers were dried (Na2SO4), decanted, and evaporated to give 14.8 g of 1-(t-butoxycarbonyl)-4-(iodomethyl)piperidine as a pale yellow oil. 1H NMR (500 MHz) δ 4.25-4.00 (m, 2H), 3.12 (d, J=4, 2H), 2.78-2.52 (m, 2H), 1.85 (d, J=13, 2H), 1.68-1.56 (m, 1H), 1.48 (s, 9H), 1.15 (qd, J=12, 4, 2H).

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 3 h
  3. customThe mixture was partitioned between ether (350 mL) and H2O (350 mL)
  4. washThe organic layer was washed with saturated aq. NaCl (250 mL)
  5. extractionthe aqueous layers were extracted in succession with ether (250 mL)
  6. dry with materialThe combined organic layers were dried (Na2SO4)
  7. customdecanted
  8. customevaporated

출처 및 근거

ORD 기록
ord-8c07d98c9a234496828ac66679a7164d
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06265434B1

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