Triethylamine → (S)-tert-butyl 2-((methylsulfonyloxy)methyl)morpholine-4-carboxylate

HRID 41100ノート

反応式

HRID 41100 の反応式
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH2:7][C@H:8]1[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]1.C(N(CC)CC)C>C(Cl)Cl.O>[CH3:1][S:2]([O:6][CH2:7][C@H:8]1[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]1)(=[O:4])=[O:3]

参加物

6

反応物 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 1512577tert-Butyl (2S)-2-(hydroxymethyl)morpholine-4-carboxylate

生成物 1

HCID 86673567(S)-tert-butyl 2-((methylsulfonyloxy)methyl)morpholine-4-carboxylate

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

実験手順

Methanesulfonyl chloride (12 mL, 0.15 mol) was added to a solution of (S)-tert-butyl 2-(hydroxymethyl)morpholine-4-carboxylate (28 g, 0.13 mmol) in CH2Cl2 (172 mL) and triethylamine (23.4 mL, 0.17 mol) at 0° C. The resulting mixture was stirred at a temperature of from 0° C. to room temperature over 1.5 hr. The mixture was then diluted with water (35 mL), and the phases were separated. The aqueous layer was extracted with CH2Cl2 (3×20 mL). The combined organic layers were washed with brine, dried over MgSO4, and filtered on a pad of silica gel, which was rinsed with CH2Cl2. The filtrate was concentrated under reduced pressure to the title product (37.7 g, 99%) as an oil. 1H NMR (300 MHz, CDCl3) δ ppm 1.55 (s, 9H), 2.77-2.91 (m, 1H), 2.97-3.09 (m, 1H), 3.14-3.15 (m, 3H), 3.57-3.67 (m, 1H), 3.73-3.81 (m, 1H), 3.85-4.10 (m, 3H), 4.31 (d, J=4.79 Hz, 2H).

後処理

  1. customthe phases were separated
  2. extractionThe aqueous layer was extracted with CH2Cl2 (3×20 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered on a pad of silica gel, which
  6. washwas rinsed with CH2Cl2
  7. concentrationThe filtrate was concentrated under reduced pressure to the title product (37.7 g, 99%) as an oil

出典と根拠

ORDレコード
ord-b8fd2c6cedd3459aa41c7ad0fe611a36
出典データセット
uspto-grants-2013_09
特許番号
US08530467B2

反応ノート

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