Dimethyl Sulfoxide → Tert-butyl 3-formylazetidine-1-carboxylate

HRID 1913147Notes

Reaction equation

HRID 1913147 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH2:12][CH:13]1[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14]1.C(N(CC)CC)C>C(Cl)Cl>[CH:12]([CH:13]1[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14]1)=[O:11]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 10583745tert-Butyl 3-(hydroxymethyl)azetidine-1-carboxylate

Product 1

HCID 10726182Tert-butyl 3-formylazetidine-1-carboxylateYield 27.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of oxalyl chloride (4.28 mL, 4.98 mmol) in DCM (5 mL) at −78° C. is added DMSO (0.71 mL, 9.96 mL) dropwise. After stirring for 15 mins tert-butyl 3-(hydroxymethyl)azetidine-1-carboxylate (0.69 g, 3.69 mmol) is added followed immediately by triethylamine (2.1 mL, 14.75 mmol). The reaction mixture is allowed to warm to room temperature, diluted with DCM (30 mL), washed with water, dried (Na2SO4), filtered and concentrated under reduced pressure. The crude product is purified by column chromatography (Isolute column, eluent: heptane, 0-100% EtOAc) to give 0.19 g of tert-butyl 3-formylazetidine-1-carboxylate (27%).

Workup

  1. additionis added
  2. washwashed with water
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product is purified by column chromatography (Isolute column, eluent: heptane, 0-100% EtOAc)

Sources & evidence

ORD record
ord-6a310ef337684be0b2f302011808cf3b
Source dataset
uspto-grants-2013_12
Patent number
US08609696B2

Reaction notes

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