Hydrochloric Acid → (R)-(6-(benzyloxy)-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methyl methanesulfonate

HRID 453766노트

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HRID 453766 반응식
[CH2:1]([O:8][C:9]1[CH:20]=[CH:19][C:12]2[O:13][C@@H:14]([CH2:17][OH:18])[CH2:15][O:16][C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30].Cl>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:20]=[CH:19][C:12]2[O:13][C@@H:14]([CH2:17][O:18][S:29]([CH3:28])(=[O:31])=[O:30])[CH2:15][O:16][C:11]=2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 66726995((S)-6-Benzyloxy-2,3-dihydrobenzo[1,4]dioxin-2-yl)methanol

생성물 1

HCID 86644715(R)-(6-(benzyloxy)-2,3-dihydrobenzo[b][1,4]dioxin-2-yl)methyl methanesulfonate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

To a stirred solution of crude ((S)-6-benzyloxy-2,3-dihydrobenzo[1,4]dioxin-2-yl)methanol (1.65 g, 6.06 mmol) in dry DCM (10 ml), was added triethylamine (0.88 ml). The mixture was cooled to 0° C. and methanesulfonyl chloride (0.49 ml) was added slowly dropwise to reaction mixture. The mixture was stirred at RT for 1 h and then 10 ml of aq 1 M HCl was added. The mixture was extracted twice with DCM. The combined organic layers were washed with water and brine, dried with Na2SO4 The solvents were removed under reduced pressure and the crude product (2.22 g) was crystallized from IPA (15 ml), which gave a white solid (1.50 g).

후처리

  1. extractionThe mixture was extracted twice with DCM
  2. washThe combined organic layers were washed with water and brine
  3. dry with materialdried with Na2SO4 The solvents
  4. customwere removed under reduced pressure
  5. customthe crude product (2.22 g) was crystallized from IPA (15 ml), which

출처 및 근거

ORD 기록
ord-93b25e03a0fd4a67a94454af19b7d1d8
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492549B2

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