Methanol → HCID 15035852、化合物

HRID 1195231ノート

反応式

HRID 1195231 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 15035852HCID 15035852、化合物

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e3177cbdb43f4d288a755964de833a61
出典データセット
uspto-grants-1992_05
特許番号
US05110933

反応ノート

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