Sodium borohydride → HCID 90424018, compound

HRID 1055168Notes

Reaction equation

HRID 1055168 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[Si:11]([O:28][CH2:29][C@@H: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.[BH4-].[Na+].C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>ClCCl.CO>[Si:11]([O:28][CH2:29][C@H: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

7

Reactant 4

HCID 4311764Sodium borohydrideHCID 9855836Potassium sodium tartarateHCID 21225700DiisobutylaluminumhydrideHCID 90423774HCID 90423774, compound

Product 1

HCID 90424018HCID 90424018, compoundYield 95.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Add diisobutylaluminum hydride (1M in hexanes; 21.65 mL; 1.6 equiv; 21.65 mmoles) to a 0° C. solution of (6R)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-5,6-dihydroimidazo[2,1-c][1,4]oxazin-8-one (5.5 g; 1.0 equiv; 13.53 mmoles) in dichloromethane (130 mL). Stir the solution for 15 minutes, then add methanol (100 mL). After 5 minutes, add sodium borohydride (0.307 g; 0.6 equiv; 8.12 mmoles) and maintain the solution at 0° C. for 15 minutes. Add saturated sodium potassium tartrate solution (80 mL) and stir the solution at ambient temperature for 14 hours. Filter the solution and separate the liquid layers. Further extract the aqueous layer with dichloromethane (3×). Wash the combined organic extracts with 50% saturated brine, dry over magnesium sulfate, filter, and concentrate to afford the desired (2R)-1-[tert-butyl(diphenyl)silyl]oxy-3-[2-(hydroxymethyl)imidazol-1-yl]propan-2-ol (5.30 g; 95%). MS (m/z): 411 (M+1).

Workup

  1. waitAfter 5 minutes
  2. filtrationFilter the solution
  3. customseparate the liquid layers
  4. extractionFurther extract the aqueous layer with dichloromethane (3×)
  5. washWash the combined organic extracts with 50% saturated brine
  6. dry with materialdry over magnesium sulfate
  7. filtrationfilter
  8. concentrationconcentrate

Sources & evidence

ORD record
ord-f8af62dbca7f461ea35b63d71334f18a
Source dataset
uspto-grants-2016_07
Patent number
US09394317B2

Reaction notes

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