Water → trans-4-(Boc-amino)cyclohexyl methanesulfonate

HRID 931481

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HRID 931481 반응식
[OH:1][CH:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:23][S:24](Cl)(=[O:26])=[O:25].O>ClCCl>[CH3:23][S:24]([O:1][CH:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])[CH2:4][CH2:3]1)(=[O:26])=[O:25]

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 1514287cis-4-(tert-Butoxycarbonylamino)cyclohexanol

생성물 1

HCID 21882613trans-4-(Boc-amino)cyclohexyl methanesulfonate수율 58%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

To a solution of tert-butyl N-(4-hydroxycyclohexyl)carbamate (3.8 g, 17.65 mmol, 1.00 equiv) and triethylamine (3.9 g, 38.54 mmol, 2.20 equiv) in dichloromethane (40 mL) was added methanesulfonyl chloride (2.43 g, 21.21 mmol, 1.21 equiv) dropwise with stirring at 0° C. The reaction mixture was stirred overnight at room temperature. Water (50 mL) was added to quench the reaction. The resulting mixture was extracted with 3×50 mL of dichloromethane. The combined organic layers was washed with 2×200 mL of brine, dried over anhydrous sodium sulfate and concentrated under vacuum to give 3.0 g (58%) of tert-butyl N-[4-(methanesulfonyloxy)cyclohexyl]carbamate as a white solid.

후처리

  1. stirringThe reaction mixture was stirred overnight at room temperature
  2. customto quench
  3. customthe reaction
  4. extractionThe resulting mixture was extracted with 3×50 mL of dichloromethane
  5. washThe combined organic layers was washed with 2×200 mL of brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-3d7252a4c91e47449365191a35706324
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296732B2

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