Triethylamine → HCID 23627687、化合物

HRID 1171907ノート

反応式

HRID 1171907 の反応式
[CH2:1]([C@@H:8]1[NH:13][CH2:12][CH2:11][N:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.C([O:42][CH2:43][C:44](Cl)=[O:45])C1C=CC=CC=1>C1COCC1.CCOC(C)=O.O.CO>[CH2:1]([C@H:8]1[CH2:9][N:10]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH:23]3[CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:15]=2)[CH2:11][CH2:12][N:13]1[C:43](=[O:42])[CH2:44][OH:45])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

8

反応物 3

HCID 8471TriethylamineHCID 177085Benzyloxyacetyl chlorideHCID 16725642(S)-3-Benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine

生成物 1

HCID 23627687HCID 23627687、化合物収率 18%

試薬・触媒・溶媒 4

HCID 887Methanol溶媒HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of (S)-3-Benzyl-1-(3-cyclopentyloxy-4-methoxy-phenyl)-piperazine (Example 2) (73 mg, 0.2 mmol) in THF (1.5 mL) at room temperature was treated with triethylamine (42 μL, 0.3 mmol) followed by benzyloxyacetyl chloride (19 μL, 0.2 mmol). The reaction mixture was stirred for 2 h then diluted with EtOAc (2 mL) and water (2 mL). The organic phase was isolated and further washed with an additional portion of a water (2 mL) followed by a brine solution (2 mL). The organic component was dried over MgSO4, filtered, and evaporated to an oil which was purified by silica gel flash chromatography with 20% then 40% EtOAc/hexane as eluant to afford coupled product as an oil (69 mg, 67%). LC/MS 7.64 min, [M+1]+ 515. The intermediate benzyloxy ether (60 mg, 0.117 mmol) was dissolved in MeOH (20 mL), purged with a stream of nitrogen, treated with 20% Pd/C (140 mg, 50% water content), and hydrogenated under 40 psi pressure of hydrogen for 4 h. The crude reaction mixture was then purged with nitrogen, filtered, evaporated, and purified by silica gel flash chromatography with 40% then 75% EtOAc/hexane as eluant to afford product as an oil (9 mg, 18%). LC/MS 6.55 min, [M+1]+ 425.

後処理

  1. customThe organic phase was isolated
  2. washfurther washed with an additional portion of a water (2 mL)
  3. dry with materialThe organic component was dried over MgSO4
  4. filtrationfiltered
  5. customevaporated to an oil which
  6. customwas purified by silica gel flash chromatography with 20%
  7. custom40% EtOAc/hexane as eluant to afford
  8. customLC/MS 7.64 min, [M+1]+ 515
  9. custompurged with a stream of nitrogen
  10. additiontreated with 20% Pd/C (140 mg, 50% water content)
  11. waithydrogenated under 40 psi pressure of hydrogen for 4 h
  12. customThe crude reaction mixture
  13. customwas then purged with nitrogen
  14. filtrationfiltered
  15. customevaporated
  16. custompurified by silica gel flash chromatography with 40%

出典と根拠

ORDレコード
ord-d8dffed339b9476db06529deff2b9284
出典データセット
uspto-grants-2010_11
特許番号
US07829713B2

反応ノート

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