Methanol → HCID 15035852, 화합물

HRID 1195231노트

반응식

HRID 1195231 반응식
[CH2:1]([N:8]1[CH2:15][CH:14]2[CH2:16][CH:10]([CH2:11][S:12][CH2:13]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[OH:18]>O>[CH2:1]([N:8]1[CH2:15][CH:14]2[CH2:16][CH:10]([CH2:11][S:12](=[O:18])[CH2:13]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 887MethanolHCID 1460497-Benzyl-3-thia-7-azabicyclo[3.3.1]nonane

생성물 1

HCID 15035852HCID 15035852, 화합물

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A 200-mL flask was equipped with a magnetic stirrer, an ice bath, and a condenser with nitrogen inlet. To a stirred, chilled (5° C.) solution of the amine (27, 1.4 g, 6 mmol) in methanol (60 mL) was added dropwise a solution of NaIO4 (1.35 g, 6.3 mmol) in water (15 mL) over 30 min. After stirring for one hour, the suspension was filtered and washed with methanol (50 mL); the washings and filtrate were combined and concentrated to a residue which was partitioned between H2CCl2 and water (40 mL each). Additional extracts (HCCl3, 3×40 mL) of the aqueous layer were combined with the initial extract, and the solution was dried (Na2SO4) and concentrated to afford an oil which solidified upon standing. Recrystallization (HCCl3 /pentane) of the solid gave 1.15 g (76.9%) of crystalline (49); mp 140°-141° C. IR (KBr) cm-1 3085, 3065, 3030, 2955, 2920, 2895, 2815, 1495, 1020, 740, 705; 1H NMR (DCCl3) δ1.59 [bd, 1H, H(9), J=13.3 Hz], 1.86 [bd, 1H, H(9), J=13.2 Hz], 2.20 [d, 2H, H(2,4)ax, J=11.7 Hz], 2.37 bs, 2H, H(1,5)], 2.62 [d, 2H, H(6,8)ax, J=12.0 Hz], 2.78 [d, 2H, H(2,4)eq, J=11.8 Hz], 3.51 [d, 2H, H(6,8)eq, J=11.7 Hz], 3.55 [s, 2H, ArCH2 ], 7.26-7.39 (m, 5H, Ar--H); 13C NMR (DCCl3) ppm 31.86 [t, C(9)], 32.59 [d, C(1,5)], 57.42 [t, C(2,4)], 58.59 [C(6,8)], 62.88 (ArCH2), 127.20, 128.39, 129.12, 137.67; 15N NMR (DCCl3) ppm 49.37 [N(7)]. Anal. Calcd. for C14H19NOS: C, 67.43; H, 7.68. Found: C, 67.61; H, 7.73.

후처리

  1. customA 200-mL flask was equipped with a magnetic stirrer, an ice bath, and a condenser with nitrogen inlet
  2. filtrationthe suspension was filtered
  3. washwashed with methanol (50 mL)
  4. concentrationconcentrated to a residue which
  5. customwas partitioned between H2CCl2 and water (40 mL each)
  6. extractioninitial extract
  7. dry with materialthe solution was dried (Na2SO4)
  8. concentrationconcentrated
  9. customto afford an oil which
  10. customRecrystallization (HCCl3 /pentane) of the solid

출처 및 근거

ORD 기록
ord-e3177cbdb43f4d288a755964de833a61
출처 데이터셋
uspto-grants-1992_05
특허 번호
US05110933

반응 노트

불러오는 중…