Sulfoxonium, trimethyl-, iodide (1:1) → tert-Butyl 1-oxa-6-azaspiro(2.5)octane-6-carboxylate

HRID 854329

反応式

HRID 854329 の反応式
[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[I-].[CH3:16][S+](C)(C)=O.CC(C)([O-])C.[Na+]>C1COCC1.COCCOC>[O:1]1[C:2]2([CH2:3][CH2:4][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:6][CH2:7]2)[CH2:16]1

参加物

5

反応物 3

HCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 23676156Sodium t-butoxide

生成物 1

HCID 22135564tert-Butyl 1-oxa-6-azaspiro(2.5)octane-6-carboxylate

試薬・触媒・溶媒 1

HCID 22732251Tetrahydrofuran dimethoxyethane溶媒

反応条件

温度
60 °C

実験手順

To a solution of tert-butyl 4-oxopiperidine-1-carboxylate (0.50 g, 2.51 mmol) in THF/DME (2:1, 6 mL) at 60° C. was added trimethylsulfoxonium iodide (0.58 g, 2.63 mmol) and sodium t-butoxide (0.25 g, 2.63 mmol). The reaction mixture was stirred at 60° C. for 30 min, cooled to rt and concentrated. Water was added and the mixture was extract with EtOAc twice. The combined organics were dried over Na2SO4, filtered and concentrated. Purification on silica gel (3:1, hexanes:EtOAc) gave tert-butyl 1-oxa-6-azaspiro[2.5]octane-6-carboxylate as a clear oil that solidified upon standing.

後処理

  1. temperaturecooled to rt
  2. concentrationconcentrated
  3. additionWater was added
  4. extractionthe mixture was extract with EtOAc twice
  5. dry with materialThe combined organics were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification on silica gel (3:1, hexanes:EtOAc)

出典と根拠

ORDレコード
ord-cae21a44277c4849a0103731f1b91da8
出典データセット
uspto-grants-2007_08
特許番号
US07259157B2

関連ノート

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