tert-Butanol → HCID 58902396, compound

HRID 1640152Notes

Reaction equation

HRID 1640152 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([CH2:14][N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)[CH:13]=1)C(O)=O)([CH3:4])([CH3:3])[CH3:2].C1[CH2:24][O:23]CC1.C1C=CC(OP(OC2C=CC=CC=2)([N:34]=[N+]=[N-])=O)=CC=1.[C:44]([OH:48])([CH3:47])([CH3:46])[CH3:45]>>[C:1]([C:5]1[CH:6]=[C:7]([NH:34][C:24](=[O:23])[O:48][C:44]([CH3:47])([CH3:46])[CH3:45])[CH:11]=[C:12]([CH2:14][N:15]2[CH2:16][CH2:17][CH2:18][CH2:19]2)[CH:13]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8028TetrahydrofuranHCID 123414Diphenylphosphoryl azideHCID 58902319HCID 58902319, compound

Product 1

HCID 58902396HCID 58902396, compound

Procedure

3-tert-butyl-5-(pyrrolidin-1-ylmethyl)benzoic acid (382 mg, 0.00146 mol) was stirred in THF (40 mL, 0.4 mol) at 0° C. for 15 minutes. To this cold solution was added diphenylphosphonic azide (0.41 mL, 0.0019 mol) and TEA (0.73 mL, 0.0053 mol). The reaction mixture was allowed to warm to rt and stir for 2 hours. The solvents were evaporated (low heat) and the residue was redissolved in EtOAc. The organic solution was washed with sat. NaHCO3 solution and brine then dried over Na2SO4, filtered, and evaporated (low heat). tert-Butyl alcohol (35.8 mL, 0.374 mol) was added to the residue and the reaction mixture was heated overnight at 85° C. under an atmosphere of nitrogen. The mixture was concentrated and the residue taken up in EtOAc. The organic solution was washed with NaOH and brine, dried over MgSO4,filtered and concentrated. The residue was purified by column chromatography using basic alumina to give tert-butyl [3-tert-butyl-5-(pyrrolidin-1-ylmethyl)phenyl]carbamate. LCMS ES+ 333.

Workup

  1. customThe solvents were evaporated
  2. temperature(low heat)
  3. dissolutionthe residue was redissolved in EtOAc
  4. washThe organic solution was washed with sat. NaHCO3 solution and brine
  5. dry with materialthen dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated
  8. temperature(low heat)
  9. temperaturethe reaction mixture was heated overnight at 85° C. under an atmosphere of nitrogen
  10. concentrationThe mixture was concentrated
  11. washThe organic solution was washed with NaOH and brine
  12. dry with materialdried over MgSO4,filtered
  13. concentrationconcentrated
  14. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-0000a856233d41ce832a4afb042d2311
Source dataset
uspto-grants-2012_02
Patent number
US08110687B2

Reaction notes

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