Réaction #58039

ord-96b54c9a3c1a42999c07ec1e126ca2be

Équation de réaction

CC(C)(C)OC(=O)N[C@H]1CC[C@H](C=NCc2ccccc2)CC1
trans-[4-(benzylimino-methyl)-cyclohexyl]-carbamic acid tert-butyl ester
O=C(O)C(=O)O
oxalic acid
→
CC(C)(C)OC(=O)N[C@H]1CC[C@H](C=O)CC1
trans-(4-Formyl-cyclohexyl)-carbamic acid tert-butyl ester
Rendement 80.0%

Réactifs

CC(C)(C)OC(=O)N[C@H]1CC[C@H](C=NCc2ccccc2)CC1
trans-[4-(benzylimino-methyl)-cyclohexyl]-carbamic acid tert-butyl ester
O=C(O)C(=O)O
oxalic acid

Réactifs

Aucun

Solvants

C1CCOC1.O
water THF

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    ConcentrationThe reaction mixture was concentrated under reduced pressure and methylene chloride (50 mL)
  2. 2
    workup.ADDITIONwas added to the residue
  3. 3
    AutreThe organic phase was dried
  4. 4
    Concentrationconcentrated under reduced pressure

Mode opératoire

A solution of trans-[4-(benzylimino-methyl)-cyclohexyl]-carbamic acid tert-butyl ester (2.50 g, 8.00 mmol) and oxalic acid (0.80 g) in water/THF (50 mL, 1:1) was stirred for 10 h at room temperature. The reaction mixture was concentrated under reduced pressure and methylene chloride (50 mL) was added to the residue. The organic phase was dried and concentrated under reduced pressure to give trans-(4-Formyl-cyclohexyl)-carbamic acid tert-butyl ester (1.3 g, 80%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07423012B2uspto-grants-2008_09