Tetrahydro-2,5-dimethoxyfuran-3-carbaldehyde → trans-[2-(3-Formyl-pyrrol-1-yl)-cyclohexyl]-carbamic acid tert-butyl ester

HRID 2218560Notes

Reaction equation

HRID 2218560 reaction equation
[C:1]([O:5][C:6](=[O:15])[NH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[NH2:14])([CH3:4])([CH3:3])[CH3:2].C[O:17][CH:18]1[CH:22]([CH:23]=O)[CH2:21][CH:20](OC)O1>N1C=CC=CC=1.C(O)(=O)C>[C:1]([O:5][C:6](=[O:15])[NH:7][C@@H:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[N:14]1[CH:20]=[CH:21][C:22]([CH:18]=[O:17])=[CH:23]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 567310Tetrahydro-2,5-dimethoxyfuran-3-carbaldehydeHCID 1514390(1R,2R)-trans-N-Boc-1,2-cyclohexanediamine

Product 1

HCID 86605566trans-[2-(3-Formyl-pyrrol-1-yl)-cyclohexyl]-carbamic acid tert-butyl esterYield 61.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1049PyridineSolvent

Procedure

A solution of trans-(2-amino-cyclohexyl)-carbamic acid tert-butyl ester (Tetrahedron Lett. 2000, 41, 9607; 400 mg, 1.87 mmol) and 2,5-dimethoxy-3-tetrahydrofurancarboxaldehyde (365 mg, 2.05 mmol) in pyridine (0.5 mL) and acetic acid (0.82 mL) was heated at 100° C. for 4.5 h. After cooling, the reaction mixture was partitioned between ethyl acetate and 10% aq. citric acid solution. The organic layer was washed with brine, dried (MgSO4), and evaporated. Chromatography (SiO2, heptane-ethyl acetate gradient) yielded the title compound (334 mg, 61%). Off-white solid, MS (ISP) 293.3 (M+H)+.

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was partitioned between ethyl acetate and 10% aq. citric acid solution
  3. washThe organic layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-c392ae0315bc4243b05878bde979704b
Source dataset
uspto-grants-2008_08
Patent number
US07411093B2

Reaction notes

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