Triethylamine → (1-Benzhydrylazetidin-3-yl)methyl methanesulfonate

HRID 10203Notes

Reaction equation

HRID 10203 reaction equation
[C:1]1([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:8]2[CH2:11][CH:10]([CH2:12][OH:13])[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(C(C2C=CC=CC=2)N2CC(C(O)=O)C2)C=CC=CC=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].CCN(CC)CC.[CH3:53][S:54](Cl)(=[O:56])=[O:55]>C1COCC1>[CH3:53][S:54]([O:13][CH2:12][CH:10]1[CH2:11][N:8]([CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[CH2:9]1)(=[O:56])=[O:55]

Participants

7

Reactant 5

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 27354401-(Diphenylmethyl)azetidine-3-carboxylic acidHCID 2758715(1-Benzhydrylazetidin-3-yl)methanolHCID 21226445Aluminium lithium hydride

Product 1

HCID 21978370(1-Benzhydrylazetidin-3-yl)methyl methanesulfonateYield 85.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-(diphenylmethyl)-3-(hydroxymethyl) azetidine (1 g, 3.9 mmol) [prepared by reduction of 1-(diphenylmethyl)azetidine-3-carboxylic acid (CAS No.: 36476-87-6) using LiAlH4 in refluxing THF] and Et3N (0.71 mL, 5.1 mmol) in THF (30 mL) was treated with methanesulfonyl chloride (0.36 mL, 4.7 mmol) and stirred for 2 h at room temperature. The precipitate was removed by filtration and washed with THF. The liquors were evaporated and the residue partitioned between water and DCM. The DCM layer was separated and the aqueous re-extracted. The combined organics were washed with brine, dried (Na2SO4), filtered and evaporated. The residue was triturated with isohexane, the solid then isolated by filtration and dried to give the title compound as an orange solid (1.1 g, 84%). m/z (ES+) 332 (M+H)+.

Workup

  1. customThe precipitate was removed by filtration
  2. washwashed with THF
  3. customThe liquors were evaporated
  4. customthe residue partitioned between water and DCM
  5. customThe DCM layer was separated
  6. washThe combined organics were washed with brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was triturated with isohexane
  11. customthe solid then isolated by filtration
  12. customdried

Sources & evidence

ORD record
ord-adf83879186b4eeab6d3dae8f4e71145
Source dataset
uspto-grants-2006_08
Patent number
US07094777B2

Reaction notes

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