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

HRID 931481

反応式

HRID 931481 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-3d7252a4c91e47449365191a35706324
出典データセット
uspto-grants-2016_03
特許番号
US09296732B2

関連ノート

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