Isopropanol → (S)-3-((R)-1-Hydroxy-2-isopropoxyethyl)pyrrolidine-1-carboxylic Acid t-Butyl Ester

HRID 533383ノート

反応式

HRID 533383 の反応式
[CH:1](O)([CH3:3])[CH3:2].[H-].[Na+].[C:7]([O:11][C:12]([N:14]1[CH2:18][CH2:17][C@H:16]([C@@H:19]2[CH2:21][O:20]2)[CH2:15]1)=[O:13])([CH3:10])([CH3:9])[CH3:8].C1C[O:25]CC1>>[C:7]([O:11][C:12]([N:14]1[CH2:18][CH2:17][C@H:16]([C@@H:19]([OH:25])[CH2:21][O:20][CH:1]([CH3:3])[CH3:2])[CH2:15]1)=[O:13])([CH3:8])([CH3:9])[CH3:10]

参加物

5

反応物 4

HCID 3776IsopropanolHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 86650334(S)-(R)-3-Oxiranylpyrrolidine-1-carboxylic acid t-butyl ester

生成物 1

HCID 66859524(S)-3-((R)-1-Hydroxy-2-isopropoxyethyl)pyrrolidine-1-carboxylic Acid t-Butyl Ester

反応条件

温度
0 °C

実験手順

Isopropyl alcohol (215 μL, 2.8 mmol) was dissolved in THF (428 μL), and the mixture was cooled at 0° C. NaH (33.8 mg, 1.4 mmol) was added in 4 portions, and the mixture stirred for 10 minutes at room temperature. (S)—(R)-3-Oxiranylpyrrolidine-1-carboxylic acid t-butyl ester (200 mg, 938 μmol) was added. The resulting solution was placed in a microwave reactor for 10 minutes at 100° C., then cooled to room temperature. The mixture was extracted with Hexanes (10 mL) and washed with water (10 mL). The organic layer was collected, dried over Na2SO4, filtered, and concentrated. The crude product was purified by column chromatography (0-100% EtOAc in hexanes) to give the title compound as a clear oil (162 mg).

後処理

  1. waitThe resulting solution was placed in a microwave reactor for 10 minutes at 100° C.
  2. temperaturecooled to room temperature
  3. extractionThe mixture was extracted with Hexanes (10 mL)
  4. washwashed with water (10 mL)
  5. customThe organic layer was collected
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by column chromatography (0-100% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-3eeb55f85ac2491db6950250859519cc
出典データセット
uspto-grants-2014_10
特許番号
US08853255B2

反応ノート

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