Dimethyl Sulfoxide → 1-Boc-4-formyl-azepane

HRID 1809635Notes

Reaction equation

HRID 1809635 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][CH2:12][CH:13]1[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15][CH2:14]1.C(N(CC)CC)C>C(Cl)Cl.O>[CH:12]([CH:13]1[CH2:19][CH2:18][CH2:17][N:16]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:15][CH2:14]1)=[O:11]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 68708706Tert-butyl 4-(hydroxymethyl)azepane-1-carboxylate

Product 1

HCID 588702361-Boc-4-formyl-azepaneYield 100.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×

Procedure

At −60° C., a solution of DMSO (1.73 ml, 24.4 mmol) in CH2Cl2 (20 mL) was added dropwise to a 2M solution of oxalyl chloride (1.28 mL, 14.7 mmol) in CH2Cl2 (7 mL). The mixture was stirred for 20 minutes and then a solution of tert-butyl 4-(hydroxymethyl)azepane-1-carboxylate (2.8 g, 12.2 mmol) in CH2Cl2 (7 mL) was added dropwise. The mixture was stirred for 10 minutes and triethylamine (8.51 ml, 61.1 mmol) was slowly added. The reaction mixture was warmed to ambient temperature and water was added. When the mixture became clear, it was extracted with CH2Cl2, the solvent evaporated to afford crude tert-butyl 4-formylazepane-1-carboxylate (2.78 g, 100%).

Workup

  1. stirringThe mixture was stirred for 10 minutes
  2. extractionit was extracted with CH2Cl2
  3. customthe solvent evaporated

Sources & evidence

ORD record
ord-c3bef9f2948143158dc62773066ae9c7
Source dataset
uspto-grants-2013_01
Patent number
US08362037B2

Reaction notes

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