Triethylamine → tert-Butyl N-(3-formylcyclohexyl)carbamate

HRID 1521948Notes

Reaction equation

HRID 1521948 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:8][CH2:7][CH2:6][CH:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:4]1.C(N(CC)CC)C.C1C=CN=CC=1.O=S(=O)=O>CS(C)=O>[CH:2]([CH:3]1[CH2:8][CH2:7][CH2:6][CH:5]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:14])([CH3:13])[CH3:15])[CH2:4]1)=[O:1]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 168533Sulfur trioxide-pyridineHCID 22106830tert-butyl N-[3-(hydroxymethyl)cyclohexyl]carbamate

Product 1

HCID 86717490tert-Butyl N-(3-formylcyclohexyl)carbamate

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

To a solution of tert-butyl 3-(hydroxymethyl)cyclohexylcarbamate (1.4 g, 6.11 mmol) in dimethylsulfoxide (10 mL) was added triethylamine (1.853 g, 18.32 mmol) followed by the pyridine-sulfur trioxide (2.92 g, 18.32 mmol) in 5 mL of dimethylsulfoxide, and the mixture was stirred at room temperature for 1 hour. The mixture was quenched with ice water and extracted into ethyl acetate (30 mL×2). The organic layer was washed with water and brine solution (25 mL each), dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford the title compound.

Workup

  1. customThe mixture was quenched with ice water
  2. extractionextracted into ethyl acetate (30 mL×2)
  3. washThe organic layer was washed with water and brine solution (25 mL each)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fcb502c26fa5490cb86f67384f79ed65
Source dataset
uspto-grants-2015_07
Patent number
US09073922B2

Reaction notes

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