HCID 68767426, compound → HCID 11472439, compound

HRID 1170949Notes

Reaction equation

HRID 1170949 reaction equation
C([O:8][C@@H:9]1[C@@H:14]([CH2:15][O:16]CC2C=CC=CC=2)[N:13]2[CH:24]=[C:25]([C:27]#[C:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[N:26]=[C:12]2[C@H:11]([O:35]CC2C=CC=CC=2)[C@H:10]1[O:43]CC1C=CC=CC=1)C1C=CC=CC=1>C1COCC1.CCO.[OH-].[OH-].[Pd+2]>[OH:16][CH2:15][C@H:14]1[N:13]2[CH:24]=[C:25]([CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[N:26]=[C:12]2[C@H:11]([OH:35])[C@@H:10]([OH:43])[C@@H:9]1[OH:8]

Participants

4

Reactant 1

HCID 68767426HCID 68767426, compound

Product 1

HCID 11472439HCID 11472439, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 21873804Tetrahydrofuran ethanolSolvent

Procedure

A solution of (5R,6R,7S,8S)-6,7,8-Tris(benzyloxy)-5-[(benzyloxy)methyl]-2-(1-octynyl)-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine (120 mg, 0.179 mmol) in THF/EtOH (2:1) (3 ml) is rapidly stirred with Pd(OH)2/C (0.1 g) under an atmosphere of hydrogen for 14 h. After filtration of the catalyst, the organic solution is concentrated on a rotovap and the residue is dissolved in CH2Cl2 (10 ml). The solution is cooled in an acetone-dry ice bath and a solution of BCl3 (1.0 M) in CH2Cl2 is slowly added. The reaction mixture is warmed room temperature and stirred for 3 hours. The reaction mixture is cooled in an ice-water bath, water added and for 0.5 hour. Most of the solvent is removed using a rotovap and the crude product is purified by chromatography (CHCl3/MeOH/H2O 64:25:4). Lyophilization from water gives the title compound as white foam. 1H NMR (400 MHz, CD3OD): δ7.22 (s, 1H), 4.56 (d, 1H, J=8 Hz), 4.20-4.16 (m, 1H), 3.98-3.93 (m, 2H), 3.83 (t, 1H, J=8.4 Hz), 3.70 (dd, 1H, J=8.8 Hz and 10 Hz), 2.60 (t, 2H, J=7.2 Hz), 1.67-1.63 (m, 2H), 1.35-1.30 (m, 10H), 0.90 (t, 3H, J=6.8 Hz). MS (ES+): 313 [M+1].

Workup

  1. filtrationAfter filtration of the catalyst
  2. concentrationthe organic solution is concentrated on a rotovap
  3. dissolutionthe residue is dissolved in CH2Cl2 (10 ml)
  4. temperatureThe solution is cooled in an acetone-dry ice bath
  5. additiona solution of BCl3 (1.0 M) in CH2Cl2 is slowly added
  6. temperatureThe reaction mixture is cooled in an ice-water bath
  7. additionwater added and for 0.5 hour
  8. customMost of the solvent is removed
  9. customthe crude product is purified by chromatography (CHCl3/MeOH/H2O 64:25:4)

Sources & evidence

ORD record
ord-34af0aa25d39469aa577b30e40bd64d3
Source dataset
uspto-grants-2010_11
Patent number
US07829579B2

Reaction notes

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