Borane;tetrahydrofuran → 2-(1-Trityl-1H-imidazol-4-yl)ethanol

HRID 76862Notes

Reaction equation

HRID 76862 reaction equation
[C:1]([N:20]1[CH:24]=[C:23]([CH2:25][C:26](O)=[O:27])[N:22]=[CH:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.C1COCC1>C1COCC1.C(CN)O.CCOC(C)=O>[C:1]([N:20]1[CH:24]=[C:23]([CH2:25][CH2:26][OH:27])[N:22]=[CH:21]1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 11090087(1-Trityl-1H-imidazol-4-yl)acetic acid

Product 1

HCID 106894902-(1-Trityl-1H-imidazol-4-yl)ethanol

Reagents, catalysts & solvents 3

HCID 700EthanolamineSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

(1-Trityl-1H-imidazol-4-yl)acetic acid (65 g, 0.17 mol) is suspended in THF (400 mL) and cooled to 0° C. To this is added BH3.THF solution (350 mL, 1.0 M). The clear solution obtained is stirred at 0° C. for 30 min before warming to room temperature until LCMS indicated completion of the reaction. The solution is cooled again to 0° C. and quenched carefully with water (250 mL). The resulting solution is diluted with EtOAc (300 mL) and transferred to a separatory funnel and the aqueous layer is extracted with EtOAc. The organic phase is dried over anhydrous Na2SO4 and evaporated to give a sticky residue which is taken up in ethanolamine (800 mL) and heated to 90° C. for 2 h. The reaction is transferred to a separatory funnel, diluted with EtOAc (1 L) and washed with water (3×600 mL). The organic phase is dried over anhydrous Na2SO4 and evaporated to give 2-(1-trityl-1H-imidazol-4-yl)-ethanol as a white solid that is used as is without further purification. MS (ESI) m/z 354.8 (M+H) (prepared by alternate method in J. Med. Chem. 1996, 39(19), 3806)

Workup

  1. customThe clear solution obtained
  2. temperaturebefore warming to room temperature until LCMS
  3. customcompletion of the reaction
  4. temperatureThe solution is cooled again to 0° C.
  5. customquenched carefully with water (250 mL)
  6. additionThe resulting solution is diluted with EtOAc (300 mL)
  7. customtransferred to a separatory funnel
  8. extractionthe aqueous layer is extracted with EtOAc
  9. dry with materialThe organic phase is dried over anhydrous Na2SO4
  10. customevaporated
  11. customto give a sticky residue which
  12. temperatureheated to 90° C. for 2 h
  13. customThe reaction is transferred to a separatory funnel
  14. washwashed with water (3×600 mL)
  15. dry with materialThe organic phase is dried over anhydrous Na2SO4
  16. customevaporated

Sources & evidence

ORD record
ord-86cf036c295542a8a466a2f4d75a1507
Source dataset
uspto-grants-2014_09
Patent number
US08835646B2

Reaction notes

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