HCID 178451417, compound → HCID 178521625, compound

HRID 1846816Notes

Reaction equation

HRID 1846816 reaction equation
[OH:1][C@H:2]1[CH2:5][C@H:4]([C:6]2[N:10](C(OC(C)(C)C)=O)[C:9]3[CH:18]=[CH:19][CH:20]=[CH:21][C:8]=3[N:7]=2)[CH2:3]1>ClCCl.C(O)(C(F)(F)F)=O>[NH:7]1[C:8]2[CH:21]=[CH:20][CH:19]=[CH:18][C:9]=2[N:10]=[C:6]1[C@H:4]1[CH2:3][C@H:2]([OH:1])[CH2:5]1

Participants

4

Reactant 1

HCID 178451417HCID 178451417, compound

Product 1

HCID 178521625HCID 178521625, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 2-(trans-3-hydroxycyclobutyl)-1H-benzo[d]imidazole-1-carboxylate (0.31 g, 1.09 mmol) was stirred in a mixture of dichloromethane (5 mL) and TFA (5 mL) at RT for 4 h, then the mixture was concentrated in vacuo. The residue was partitioned between saturated aqueous sodium bicarbonate solution and 10:1 DCM/MeOH the layers were separated and the aqueous layer was extracted with 10:1 DCM/MeOH (3×). The combined extracts were dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give trans-3-(1H-benzo[d]imidazol-2-yl)cyclobutanol (0.11 g, 0.58 mmol, 54% yield) as a white solid.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customThe residue was partitioned between saturated aqueous sodium bicarbonate solution and 10:1 DCM/MeOH the layers
  3. customwere separated
  4. extractionthe aqueous layer was extracted with 10:1 DCM/MeOH (3×)
  5. dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-74edcc585d684cf69dc865e2098dcb84
Source dataset
uspto-grants-2015_02
Patent number
US08952037B2

Reaction notes

Loading…