Sodium Imidazole → HCID 67804705, compound

HRID 2399578Notes

Reaction equation

HRID 2399578 reaction equation
[CH3:1][O:2][C@@H:3]1[C@:8]2([O:10][CH2:9]2)[C@H:7](/[CH:11]=[CH:12]/[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[O:6][CH2:5][C@@H:4]1[CH3:20].[CH:21]1[N-:25][CH:24]=[N:23][CH:22]=1.[Na+]>CN(C)C=O.O>[N:23]1([CH2:9][C@:8]2([OH:10])[C@@H:3]([O:2][CH3:1])[C@@H:4]([CH3:20])[CH2:5][O:6][C@H:7]2/[CH:11]=[CH:12]/[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH:22]=[CH:21][N:25]=[CH:24]1

Participants

5

Reactant 2

HCID 4605971Sodium ImidazoleHCID 22855995HCID 22855995, compound

Product 1

HCID 67804705HCID 67804705, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of (3S,4S,7S,8S)-8-methoxy-7-methyl-4-[(E)-1-nonenyl]-1,5-dioxaspiro[2,5]octane (4.2 mg) and imidazole sodium derivative (14.0 mg) in dry N,N-dimethylformamide(0.5 ml) was stirred for 15 hours at room temperature. The reaction mixture was diluted with water. The mixture was extracted with dietyl ether, the combined ethereal extracts were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated. Purification of the residue by preparative thin layer chromatography (ethyl acetate as an eluent) gave (2S,3S,4S,5S)-3-(1H-imidazol-1-ylmethyl)-4-methoxy-5-methyl-2-[(E)-1-nonenyl]tetrahydro-2H-pyran-3-ol (4.1 mg, y. 79%) as colorless oil; EI-MS: m/z 351 (M+); 1H-NMR (CDCl3)d: 0.88 (3H,t,J=8 Hz), 1.10 (3H,d,J=7 Hz), 1.2-1.5 (10H,m), 2.1 (3H,m), 2.39 (1H,br.s, --OH), 2.93 (1H,d,J=5 Hz), 3.39 (3H,s), 3.40 (1H, dd, J=3 & 12 Hz), 3.61 (1H,d,J=8 Hz), 3.76 (1H,dd,J=4 & 12 Hz), 3.96 (1H,d,J=14 Hz), 4.13 (1H,d,J=14 Hz), 5.87 (2H,m), 6.91 (1H, s), 7.14 (1H,s), 7.46 (1H,s).

Workup

  1. extractionThe mixture was extracted with dietyl ether
  2. washthe combined ethereal extracts were washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification of the residue by preparative thin layer chromatography (ethyl acetate as an eluent)

Sources & evidence

ORD record
ord-8706167efe034c2996818a44a784b6d2
Source dataset
uspto-grants-1995_09
Patent number
US05449785

Reaction notes

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