Methanol → HCID 15035852, compound

HRID 1195231Notes

Reaction equation

HRID 1195231 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

HCID 15035852HCID 15035852, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e3177cbdb43f4d288a755964de833a61
Source dataset
uspto-grants-1992_05
Patent number
US05110933

Reaction notes

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