Methanol → HCID 90423990, compound

HRID 1055163Notes

Reaction equation

HRID 1055163 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[Si:11]([O:28][CH2:29][CH:30]1[O:35][C:34](=[O:36])[C:33]2=[N:37][CH:38]=[CH:39][N:32]2[CH2:31]1)([C:24]([CH3:27])([CH3:26])[CH3:25])([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.CO.[BH4-].[Na+]>ClCCl>[Si:11]([O:28][CH2:29][CH:30]([OH:35])[CH2:31][N:32]1[CH:39]=[CH:38][N:37]=[C:33]1[CH2:34][OH:36])([C:24]([CH3:26])([CH3:27])[CH3:25])([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 21225700DiisobutylaluminumhydrideHCID 90424176HCID 90424176, compound

Product 1

HCID 90423990HCID 90423990, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Add diisobutylaluminum hydride (35 mL; 1M in hexanes; 1.5 equiv; 35 mmoles) to a 0° C. solution of 6-[[tert-butyl(diphenyl)silyl]oxymethyl]-5,6-dihydroimidazo[2,1-c][1,4]oxazin-8-one (9.48 g; 1.0 equiv; 23.32 mmoles) in dichloromethane (200 mL). Stir the solution for 15 minutes, then add methanol (150 mL). After 5 minutes, add sodium borohydride (0.176 g; 0.2 equiv; 4.66 mmoles) and maintain the solution at 0° C. for 15 minutes. Add saturate sodium potassium tartrate (50 mL) and stir the solution at ambient temperature for 20 minutes. Concentrate the solution to ˜100 mL, add water and dichloromethane (100 mL each), and separate the layers. Further extract the aqueous layer with dichloromethane (5×). Dry the combined organic extracts over magnesium sulfate, filter, and concentrate to afford the desired 1-[tert-butyl(diphenyl)silyl]oxy-3-[2-(hydroxymethyl)imidazol-1-yl]propan-2-ol (9.40 g; 98%). MS (m/z): 411 (M+1).

Workup

  1. waitAfter 5 minutes
  2. additionAdd
  3. concentrationsaturate sodium potassium tartrate (50 mL)
  4. stirringstir the solution at ambient temperature for 20 minutes
  5. concentrationConcentrate the solution to ˜100 mL
  6. additionadd water and dichloromethane (100 mL each)
  7. customseparate the layers
  8. extractionFurther extract the aqueous layer with dichloromethane (5×)
  9. dry with materialDry the combined organic extracts over magnesium sulfate
  10. filtrationfilter
  11. concentrationconcentrate

Sources & evidence

ORD record
ord-7cd529ae31d04f22a79a5e72e73f24ba
Source dataset
uspto-grants-2016_07
Patent number
US09394317B2

Reaction notes

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