Hydrochloric Acid → (2R*,4S*)-2-Benzyl-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine

HRID 264611

反応式

HRID 264611 の反応式
Cl.[CH2:2]([C@@H:9]1[CH2:14][C@@H:13]([N:15]([CH2:22][C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:26]=[CH:25][CH:24]=2)[C:16](=[O:21])[C:17]([F:20])([F:19])[F:18])[CH2:12][CH2:11][N:10]1C(OC(C)(C)C)=O)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1>O1CCOCC1>[CH2:2]([C@@H:9]1[CH2:14][C@@H:13]([N:15]([CH2:22][C:23]2[C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[N:26]=[CH:25][CH:24]=2)[C:16](=[O:21])[C:17]([F:19])([F:20])[F:18])[CH2:12][CH2:11][NH:10]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 57080478(2R*,4S*)-2-Benzyl-1-t-butyloxycarbonyl-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine

生成物 1

HCID 57202094(2R*,4S*)-2-Benzyl-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

250 ml of 6N hydrogen chloride in dioxane is added dropwise over the course of 3 minutes to 7.73 g (14.7 mmol) of (2R*,4S*)-2-benzyl-1-t-butyloxycarbonyl-N-(4-quinolylmethyl)-N-trifluoroacetyl-4-piperidinamine while cooling in ice, and the mixture is subsequently stirred at room temperature for 1 hour. The reaction mixture is concentrated in a rotary evaporator, basified with 1N sodium bicarbonate solution and extracted with methylene chloride. The organic phases are dried over magnesium sulfate and evaporated to dryness. The brownish oil (7.14 g) is chromatographed on silica gel with methylene chloride/methanol/conc. ammonia (700:50:1). The title compound is obtained as yellow oil. TLC: methylene chloride/methanol/conc. ammonia (700:50:1) Rf =0.42, DCI-MS: (M+H)+ =428, IR: 1690 cm-1.

後処理

  1. temperaturewhile cooling in ice
  2. concentrationThe reaction mixture is concentrated in a rotary evaporator
  3. extractionextracted with methylene chloride
  4. dry with materialThe organic phases are dried over magnesium sulfate
  5. customevaporated to dryness
  6. customThe brownish oil (7.14 g) is chromatographed on silica gel with methylene chloride/methanol/conc

出典と根拠

ORDレコード
ord-8e468c60108c4e59a886aa52b72926a8
出典データセット
uspto-grants-1997_07
特許番号
US05646144

関連ノート

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