1,8-Diazabicyclo(5.4.0)undec-7-ene → methyl (4R)-4-{[(tert-butoxy)carbonyl]amino}cyclopent-1-ene-1-carboxylate

HRID 571349Notes

Reaction equation

HRID 571349 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:13][C@@H:12]([C:14]([O:16][CH3:17])=[O:15])[CH:11]=[CH:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1CCN2C(=NCCC2)CC1>C(Cl)Cl>[CH3:17][O:16][C:14]([C:12]1[CH2:13][C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:10][CH:11]=1)=[O:15]

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 10610130(1R,4S)-methyl 4-(tert-butoxycarbonylamino)cyclopent-2-enecarboxylate

Product 1

HCID 10586185methyl (4R)-4-{[(tert-butoxy)carbonyl]amino}cyclopent-1-ene-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of the product from Step A (9.8 g, 40.6 mmol) and DBU (9 mL, 60 mmol) in DCM (70 mL) was stirred at rt overnight. The mixture was cooled to 0° C. and washed with 1N HCl aqueous solution and brine, dried over Na2SO4. Evaporation and purification by column chromatography (eluent: 20% EtOAc in hexanes to 40%) gave the product as a white solid. 1H-NMR (400 MHz, CDCl3): δ 1.44 (s, 9H), 2.36-2.47 (m, 2H), 2.88-2.99 (m, 2H), 3.74 (s, 3H), 4.36 (br s, 1H), 4.71 (br s, 1H), 6.71-6.72 (m, 1H). LC/MS: C12H19NO4: m/z 264.0 (M+Na).

Workup

  1. temperatureThe mixture was cooled to 0° C.
  2. washwashed with 1N HCl aqueous solution and brine
  3. dry with materialdried over Na2SO4
  4. customEvaporation and purification by column chromatography (eluent: 20% EtOAc in hexanes to 40%)

Sources & evidence

ORD record
ord-024f9b135f9943ecafddf68c0cb48029
Source dataset
uspto-grants-2015_05
Patent number
US09024017B2

Reaction notes

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