Triethylamine → {1-[(Benzyloxy)methyl]cyclopropyl}methyl methanesulfonate

HRID 2279894노트

반응식

HRID 2279894 반응식
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[CH2:6]([O:13][CH2:14][C:15]1([CH2:18][OH:19])[CH2:17][CH2:16]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(N(CC)CC)C>ClCCl>[CH3:1][S:2]([O:19][CH2:18][C:15]1([CH2:14][O:13][CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:16][CH2:17]1)(=[O:4])=[O:3]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 19697866{1-[(Benzyloxy)methyl]cyclopropyl}methanol2회

생성물 1

HCID 86697829{1-[(Benzyloxy)methyl]cyclopropyl}methyl methanesulfonate수율 77.6%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Methane sulfonyl chloride (5.2 mL, 68.7 mmol) was added drop wise to an ice cooled solution of {1-[(benzyloxy)methyl]cyclopropyl}methanol (Compound 63E, 11 g, 57.2 mmol) and triethylamine (15.5 mL, 114 mmol) in dichloromethane (50 mL). The reaction mixture warmed to RT and allowed to stir overnight. The reaction mixture was filtered to remove solids. The filtrate was washed with saturated sodium bicarbonate solution followed by brine, dried over magnesium sulfate, filtered and concentrated to give 12 g (77%) of the desired product as light yellow oil which was used without further purification. 1H NMR (400 MHz, CDCl3) δ 7.25-7.41 (m, 5H), 4.58 (s, 2H), 4.21 (s, 2H), 3.42 (s, 2H), 2.96 (s, 3H), 0.61-0.75 (m, 4H).

후처리

  1. filtrationThe reaction mixture was filtered
  2. customto remove solids
  3. washThe filtrate was washed with saturated sodium bicarbonate solution
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-54db408fcd7d4789bf42f0030e5ea64e
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133224B2

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