1,2-Dichloroethane → HCID 57744213、化合物

HRID 1685115ノート

反応式

HRID 1685115 の反応式
[OH:1][CH2:2][C@H:3]1[NH:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1.[C:16](O)(=O)[CH3:17].C(O[BH-](O[C:30](=O)[CH3:31])OC(=O)C)(=O)C.[Na+].[C:34](=O)(O)[O-].[Na+].Cl[CH2:40][CH2:41]Cl>>[CH2:34]([N:8]1[CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4][C@H:3]1[CH2:2][OH:1])[C:16]1[CH:17]=[CH:31][CH:30]=[CH:41][CH:40]=1

参加物

6

反応物 5

HCID 111,2-DichloroethaneHCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 24820294tert-butyl (3S)-3-(hydroxymethyl)piperazine-1-carboxylate

生成物 1

HCID 57744213HCID 57744213、化合物収率 84%

反応条件

温度
0 °C

実験手順

Into a 250 mL round bottom flask was added 15L (10.93 g, 50.5 mmol) and 1,2-dichloroethane (144 mL). Acetic acid (3.03 g, 1 eq) was added and the flask was cooled to 0° C. Sodium triacetoxyborohydride (13.91 g, 1.3 eq) was slowly added. The flask was warmed to room temperature and stirred overnight at room temperature. The reaction mixture was poured onto saturated sodium bicarbonate. The organic layer was separated and the aqueous was extracted two times with ethyl acetate. The organic were combined and washed once with brine. The organics were dried over sodium sulfate and filtered. Solvent was removed under vacuum. The residue was purified by column chromatography with 50% ethyl acetate in hexanes to give a white solid 15N (13.07 g, 84%).

後処理

  1. temperatureThe flask was warmed to room temperature
  2. customThe organic layer was separated
  3. extractionthe aqueous was extracted two times with ethyl acetate
  4. washwashed once with brine
  5. dry with materialThe organics were dried over sodium sulfate
  6. filtrationfiltered
  7. customSolvent was removed under vacuum
  8. customThe residue was purified by column chromatography with 50% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-0ab41b2f42ef4d139020bc38113728dd
出典データセット
uspto-grants-2012_04
特許番号
US08148367B2

反応ノート

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