Ethyl Acetate → (R)-Tert-butyl 2-methylazetidine-1-carboxylate

HRID 10392

反応式

HRID 10392 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH2:10][C@H:9]1[CH2:12]OS(C)(=O)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([BH-](CC)CC)C.[Li+].C(OCC)(=O)C>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH2:10][C@H:9]1[CH3:12])=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 8857Ethyl AcetateHCID 23664628LithiumtriethylborohydrideHCID 59371380tert-Butyl (S)-2-(((methylsulfonyl)oxy)methyl)azetidine-1-carboxylate

生成物 1

HCID 57784717(R)-Tert-butyl 2-methylazetidine-1-carboxylate収率 30%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

2-(S)-Methanesulfonyloxymethyl-azetidine-1-carboxylic acid tert-butyl ester was (4.83 g, 18.2 mmol) was taken up in THF (11 mL), cooled to 0° C. under N2, treated drop-wise with a lithium triethylborohydride (1.0 M in THF, 73 mL), stirred at ambient temperature for 6 hours, treated with ethyl acetate (500 mL), washed with water, washed with 0.25 M HCl, washed with NaHCO3 solution, washed with brine (2×), dried (MgSO4), filtered, concentrated and purified by chromatography on silica gel eluting with a gradient of 10:1 and then 5:1 hexane:ethyl acetate to provide 0.95 g (30%) of the title compound. 1H NMR (300 MHz, CDCl3) δ 1.37 (d, J=6.10 Hz, 3 H) 1.44 (s, 9 H) 1.76 (m, 1 H) 2.27 (m, 1 H) 3.81 (t, J=7.46 Hz, 2 H) 4.28 (m, 1 H).

後処理

  1. washwashed with water
  2. washwashed with 0.25 M HCl
  3. washwashed with NaHCO3 solution
  4. washwashed with brine (2×)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by chromatography on silica gel eluting with a gradient of 10:1

出典と根拠

ORDレコード
ord-98a2701b80cf40f4b520ee3818c90065
出典データセット
uspto-grants-2006_08
特許番号
US07094790B2

関連ノート

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