Triethylamine → (2R)-1-Boc-2-(methanesulfonyloxymethyl)azetidine

HRID 553027노트

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HRID 553027 반응식
[C:1]([N:8]1[CH2:11][CH2:10][C@@H:9]1[CH2:12][OH:13])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23]>C1COCC1>[C:1]([N:8]1[CH2:11][CH2:10][C@@H:9]1[CH2:12][O:13][S:22]([CH3:21])(=[O:24])=[O:23])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 11074142(R)-1-Boc-2-azetidinemethanol

생성물 1

HCID 11140030(2R)-1-Boc-2-(methanesulfonyloxymethyl)azetidine수율 38%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

A mixture of (2R)-1-Boc-2-(hydroxymethyl)azetidine (1.5 g, 8.0 mmol; see Tetrahedron Asym. 1998, 9, 2791) and triethylamine (3.5 g, 35 mmol; Spectrum) in dry THF (20 mL) was cooled to 0° C., and methanesulfonyl chloride (0.75 mL, 9.7 mmol; Aldrich) was added slowly with stirring. The reaction mixture was allowed to warm to room temperature and stir for 1 hour, then the solid was removed by filtration and the organic phase was concentrated. The residue was dissolved in dichloromethane (40 mL), washed with water (20 mL), and then concentrated to afford the title compound (800 mg. 3.0 mmol; 38% yield). MS (DCI/NH3): 266 (M+1)+, 283 (M+18)+.

후처리

  1. temperatureto warm to room temperature
  2. stirringstir for 1 hour
  3. customthe solid was removed by filtration
  4. concentrationthe organic phase was concentrated
  5. dissolutionThe residue was dissolved in dichloromethane (40 mL)
  6. washwashed with water (20 mL)
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-d81b9abca4d148baa99c807c01aa2f6e
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07951791B2

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