Triethylamine → HCID 57542654, compound

HRID 2080299Notes

Reaction equation

HRID 2080299 reaction equation
O[CH2:2][C@H:3]1[CH2:6][CH2:5][N:4]1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8].CCN(CC)CC.CS(Cl)(=O)=O.[N-:26]=[N+:27]=[N-:28].[Na+]>C1COCC1.[Cl-].[Na+].O.CCOC(C)=O>[N:26]([CH2:2][C@H:3]1[CH2:6][CH2:5][N:4]1[C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[N+:27]=[N-:28]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 11074142(R)-1-Boc-2-azetidinemethanol

Product 1

HCID 57542654HCID 57542654, compoundYield 87.1%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a mixture of (R)-tert-butyl 2-(hydroxymethyl)azetidine-1-carboxylate (32.5 g, 173 mmol) and Et3N (27 mL, 191 mmol) in THF (650 mL) at 0° C. was added methane sulfonylchloride (14.9 ml, 191 mmol) dropwise. The mixture was stirred for 10 min. The precipitation was filtered off and the filtrate was concentrated. The residue was then dissolved with DMF (200 mL). Sodium azide (34 g, 519 mmol) was then added. The mixture was stirred at 65° C. for 6 hours. 300 mL EtOAc and 300 mL brine were then added to the reaction mixture. The organic layer was dried and concentrated. The residue was purified by Biotage silica gel chromatography (EtOAc:Hexane 1:4) to give (R)-tert-butyl 2-(azidomethyl)azetidine-1-carboxylate as a colorless oil (32 g, 87% yield). LRMS (M−100+H+) m/z 113.1.

Workup

  1. customThe precipitation
  2. filtrationwas filtered off
  3. concentrationthe filtrate was concentrated
  4. dissolutionThe residue was then dissolved with DMF (200 mL)
  5. stirringThe mixture was stirred at 65° C. for 6 hours
  6. customThe organic layer was dried
  7. concentrationconcentrated
  8. customThe residue was purified by Biotage silica gel chromatography (EtOAc:Hexane 1:4)

Sources & evidence

ORD record
ord-0c98ebcd14c141b4a2321c426be66049
Source dataset
uspto-grants-2011_04
Patent number
US07932270B2

Reaction notes

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