Oxalic Acid → HCID 178453955, compound

HRID 899063Notes

Reaction equation

HRID 899063 reaction equation
[C:1]([O:5][C:6](=[O:23])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([CH:14]=NCC2C=CC=CC=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C(O)(=O)C(O)=[O:26]>O.C1COCC1>[C:1]([O:5][C:6](=[O:23])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([CH:14]=[O:26])[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 971Oxalic AcidHCID 178453946HCID 178453946, compound

Product 1

HCID 178453955HCID 178453955, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

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%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure and methylene chloride (50 mL)
  2. additionwas added to the residue
  3. customThe organic phase was dried
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5f0dafce37674d00b2ccedf4bf4608ff
Source dataset
uspto-grants-2008_04
Patent number
US07354895B1

Reaction notes

Loading…