Hydrochloric Acid → (R)-Benzyl (5-oxotetrahydrofuran-3-yl)carbamate

HRID 731552

反応式

HRID 731552 の反応式
[BH4-].[Na+].O=[C:4]1[C@H:8]([NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:7][C:6](=[O:20])[O:5]1.Cl.C(O)C>C1COCC1.[Cl-].[Na+].O>[O:20]=[C:6]1[O:5][CH2:4][C@H:8]([NH:9][C:10](=[O:19])[O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:7]1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 4311764Sodium borohydrideHCID 12416472(R)-Benzyl (2,5-dioxotetrahydrofuran-3-yl)carbamate

生成物 1

HCID 697924(R)-Benzyl (5-oxotetrahydrofuran-3-yl)carbamate収率 51.1%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 57417360Sodium chloride; water溶媒

反応条件

温度
0 °C

実験手順

A suspension of NaBH4 (2.71 g, 71.5 mmol) in THF (50 mL) was cooled to 0° C., treated dropwise with a solution of EXAMPLE 21A (16.21 g, 65.0 mmol) in THF (50 mL), allowed to warm to room temperature, and stirred for 2 hours. The resulting mixture was treated with concentrated HCl (13.1 mL) and ethanol (13.1 mL), heated to reflux for 12 hours, allowed to cool to room temperature, poured into brine (100 mL) and the layers were separated. The aqueous phase was extracted with ethyl acetate and the combined organic layers were washed with water and brine, dried (MgSO4), filtered, and concentrated. The concentrate was triturated with diethyl ether (50 mL) for 2 hours, cooled overnight, and the solid collected by filtration to provide the desired product (7.81 g, 51%).

後処理

  1. temperatureto warm to room temperature
  2. temperatureheated
  3. temperatureto reflux for 12 hours
  4. temperatureto cool to room temperature
  5. customthe layers were separated
  6. extractionThe aqueous phase was extracted with ethyl acetate
  7. washthe combined organic layers were washed with water and brine
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe concentrate was triturated with diethyl ether (50 mL) for 2 hours
  12. temperaturecooled overnight
  13. filtrationthe solid collected by filtration

出典と根拠

ORDレコード
ord-8addecd12fac44649e93f644e206c2b7
出典データセット
uspto-grants-2009_09
特許番号
US07585858B2

関連ノート

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