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

HRID 10203노트

반응식

HRID 10203 반응식
[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]

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-adf83879186b4eeab6d3dae8f4e71145
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07094777B2

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