Trifluoroacetic acid → (S)-1-[1-(tetrahydropyran-3-yl)-1H-benzoimidazol-2-yl]ethylamine

HRID 242833Notes

Reaction equation

HRID 242833 reaction equation
C(OC(=O)[NH:7][C@H:8]([C:10]1[N:14]([CH:15]2[CH2:20][CH2:19][CH2:18][O:17][CH2:16]2)[C:13]2[CH:21]=[CH:22][CH:23]=[CH:24][C:12]=2[N:11]=1)[CH3:9])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[O:17]1[CH2:18][CH2:19][CH2:20][CH:15]([N:14]2[C:13]3[CH:21]=[CH:22][CH:23]=[CH:24][C:12]=3[N:11]=[C:10]2[C@@H:8]([NH2:7])[CH3:9])[CH2:16]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68157558{(S)-1-[1-(Tetrahydropyran-3-yl)-1H-benzoimidazol-2-yl]ethyl}carbamic acid tertbutyl ester

Product 1

HCID 68157342(S)-1-[1-(tetrahydropyran-3-yl)-1H-benzoimidazol-2-yl]ethylamineYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of {(S)-1-[1-(tetrahydropyran-3-yl)-1H-benzoimidazol-2-yl]ethyl}carbamic acid tertbutyl ester (720 mg, 2.08 mmol) in DCM (5 mL) was added TFA (15 mL) and the mixture was stirred at RT for 20 min. Volatiles were removed under reduced pressure and the resulting residue was partitioned between DCM and a saturated solution of NaHCO3. The aqueous phase was further extracted with DCM (×2) and the combined organic layers were dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% 2M NH3/MeOH in DCM). The product containing fractions were concentrated in vacuo affording (S)-1-[1-(Tetrahydropyran-3-yl)-1H-benzoimidazol-2-yl]ethylamine as an oil (305 mg, 60%). LCMS: RT 1.85 min [M−NH2]+ 229.1.

Workup

  1. customVolatiles were removed under reduced pressure
  2. customthe resulting residue was partitioned between DCM
  3. extractionThe aqueous phase was further extracted with DCM (×2)
  4. dry with materialthe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by column chromatography (Si—PCC, gradient 0-10% 2M NH3/MeOH in DCM)
  7. additionThe product containing fractions
  8. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-fbe16952fe61489185fb49ec303ef3f7
Source dataset
uspto-grants-2014_02
Patent number
US08653089B2

Reaction notes

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