3-Oxo-azetidine-1-carboxylic acid tert-butyl ester → tert-Butyl 3-methylideneazetidine-1-carboxylate

HRID 605684ノート

反応式

HRID 605684 の反応式
[CH3:1]C(C)([O-])C.[K+].[Br-].CP(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O=[C:29]1[CH2:32][N:31]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:30]1>C(OCC)C>[CH2:1]=[C:29]1[CH2:32][N:31]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:30]1

参加物

5

反応物 3

HCID 15194043-Oxo-azetidine-1-carboxylic acid tert-butyl esterHCID 23665647Potassium tert-butoxideHCID 178503020HCID 178503020、化合物

生成物 1

HCID 55269097tert-Butyl 3-methylideneazetidine-1-carboxylate収率 100%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

A mixture of potassium tert-butoxide (15.5 g, 137 mmol) and methyltriphenylphosphine bromide (49 g, 137 mmol) in diethyl ether (300 mL) was stirred at room temperature for 1 hour, followed by the addition of 1,1-dimethylethyl 3-oxoazetidine-1-carboxylate (10 g, 58 mmol in 100 mL diethyl ether). The mixture was stirred at 35° C. for 2 hours and then allowed to cool to room temperature. The mixture was filtered through a pad of celite, washing with diethyl ether. The filtrate was partitioned with water and washed twice with water, brine, dried over sodium sulfate, filtered and concentrated in vacuo to give an orange oil which was purified by column chromatography. Eluting with 10% ethyl acetate in hexanes, isolated product was concentrated in vacuo to afford 9.80 g, 58 mmol (100%) of 1,1-dimethylethyl 3-methylideneazetidine-1-carboxylate as a colorless oil. 1H NMR (400 MHz, DMSO): 5.05-4.85 (m, 2H), 4.95-4.63 (m, 4H), 1.45 (s, 9H). GC-MS for C9H15NO2: 169.

後処理

  1. stirringThe mixture was stirred at 35° C. for 2 hours
  2. temperatureto cool to room temperature
  3. filtrationThe mixture was filtered through a pad of celite
  4. washwashing with diethyl ether
  5. customThe filtrate was partitioned with water
  6. washwashed twice with water, brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto give an orange oil which
  11. customwas purified by column chromatography
  12. washEluting with 10% ethyl acetate in hexanes
  13. customisolated product
  14. concentrationwas concentrated in vacuo

出典と根拠

ORDレコード
ord-873202ec9d6a4bae9bec1d683c0d81dc
出典データセット
uspto-grants-2011_03
特許番号
US07915250B2

反応ノート

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