Ammonia → HCID 10108025, compound

HRID 2293924Notes

Reaction equation

HRID 2293924 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@H:11]2[CH2:15][C@@H:14]([OH:16])[CH:13]=[CH:12]2)=[C:4](Cl)[N:3]=1.C[N+]1([O-])CC[O:22]CC1.[NH3:26].C1COCC1.[OH2:32]>CO.[Os](=O)(=O)(=O)=O>[NH2:26][C:4]1[N:3]=[C:2]([Cl:1])[N:10]=[C:9]2[C:5]=1[N:6]=[CH:7][N:8]2[C@@H:11]1[CH2:12][C@H:13]([OH:32])[C@@H:14]([OH:16])[C@H:15]1[OH:22]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 82029Methyl morpholine oxideHCID 21881883Oxolane--water (1/1)HCID 57055623HCID 57055623, compound

Product 1

HCID 10108025HCID 10108025, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 48 (1 g, 3.70 mmol) in THF-H2O (10:1, 50 mL) was added a 60% aqueous solution of N-Methylmorpholine N-oxide (1.2 mL, 1.14 mmol) and then osmium tetroxide (30 mg). The reaction mixture was stirred at room temperature for 24 h. The solvent was removed by rotary evaporation and the residue was co-evaporated with EtOH (3×50 mL) to give a gummy material. This residue was dissolved in MeOH presaturated with anhydrous ammonia (50 mL) and stirred in a sealed tube at room temperature for 5 days. Volatiles were removed by rotary evaporation and the residue was subjected to column chromatography on silica gel (MeOH--CH2Cl2, 9:1) to give 50 (800 mg, 80%) as white solid: mp 180° C. (dec.); 1H NMR (DMSO-d6) δ 1.77-190 (m, 1 H, H-5'), 2.50 (m, 1 H, H-5') 3.75 (m, 1 H, H-2'), 3.89 (m, 1 H, H-1'), 4.40-4.52 (m, 1 H, H-3'), 4.62-4.81 (m, 1 H, H-4'), 4.87 (d, 1 H, J=3.6 Hz, OH), 5.01 (d, 1 H, J=6.6 Hz, OH), 5.36 (d, 1 H, J=4.8 Hz, OH), 7.22 (s, 2 H, NH2), 8.11 (s, 1 H, H-8).

Workup

  1. customThe solvent was removed by rotary evaporation
  2. customto give a gummy material
  3. stirringstirred in a sealed tube at room temperature for 5 days
  4. customVolatiles were removed by rotary evaporation

Sources & evidence

ORD record
ord-4134fe452eb042f7b0fd3d49a9997cf7
Source dataset
uspto-grants-1997_11
Patent number
US05688774

Reaction notes

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