1-(1-trityl-1H-imidazol-4-yl)cyclopropanol → 1-(1H-imidazol-5-yl)cyclopropan-1-ol

HRID 532903Notes

Reaction equation

HRID 532903 reaction equation
C([N:20]1[CH:24]=[C:23]([C:25]2([OH:28])[CH2:27][CH2:26]2)[N:22]=[CH:21]1)(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>C(O)=O>[NH:20]1[CH:24]=[C:23]([C:25]2([OH:28])[CH2:27][CH2:26]2)[N:22]=[CH:21]1

Participants

3

Reactant 1

HCID 867113491-(1-trityl-1H-imidazol-4-yl)cyclopropanol

Product 1

HCID 1785152401-(1H-imidazol-5-yl)cyclopropan-1-olYield 0.1%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

A mixture of 1-(1-trityl-1H-imidazol-4-yl)cyclopropanol (2.4 g, 6.55 mol) was treated with a 90% aq. solution of formic acid (50 mL) and the mixture was stirred at RT for 24 h. The mixture was then concentrated in vacuo, diluted in a small volume of MeOH, and the solution was rendered basic with a 7M solution of NH3 in MeOH. The white precipitate was filtered off and the filtrate was concentrated in vacuo. Purification by flash chromatography (SiO2, DCM/MeOH 100:0 to 85:15) afforded the title compound (920 mg). UPLC-MS: MS 125.1 (M+H+).

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. additiondiluted in a small volume of MeOH
  3. filtrationThe white precipitate was filtered off
  4. concentrationthe filtrate was concentrated in vacuo
  5. customPurification by flash chromatography (SiO2, DCM/MeOH 100:0 to 85:15)

Sources & evidence

ORD record
ord-6dece294ee124c098a664189dcb88f5a
Source dataset
uspto-grants-2014_10
Patent number
US08853203B2

Reaction notes

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