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

HRID 553027ノート

反応式

HRID 553027 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-d81b9abca4d148baa99c807c01aa2f6e
出典データセット
uspto-grants-2011_05
特許番号
US07951791B2

反応ノート

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