Triethylamine → Tert-butyl 4-carbamoyl-4-phenylpiperidine-1-carboxylate

HRID 1682963ノート

反応式

HRID 1682963 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:14](O)=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:25](CC)CC)C.C(OC(Cl)=O)C(C)C>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([C:14]([NH2:25])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 7369171-((Tert-butoxy)carbonyl)-4-phenylpiperidine-4-carboxylic acid

生成物 1

HCID 22741801Tert-butyl 4-carbamoyl-4-phenylpiperidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-10 °C

実験手順

1-tert-Butoxycarbonyl-4-phenyl-piperidine-4-carboxylic acid (1.22 g, 4 mmol) was combined with THF (40 mL) and cooled to -10° C. Triethylamine (0.61 mL, 4.4 mmol, 1.1 eq.) and isobutylchloroformate (0.57 mL, 4.4 mmol, 1.1 eq.) were added and the reaction was allowed to warm to ambient temperature and stir 15 h. The slurry was filtered and the solids were rinsed with THF. The filtrate was cooled to -10° C. and sparged with NH3 (gas) for 0.5 h. The slurry was allowed to warm to 20° C. and stir for 15 h. The slurry was filtered and the filtrate was diluted with ethyl acetate and washed with saturated NaHCO3 (3X). The organic phase was dried over MgSO4, filtered, and concentrated in vacuo to give a residue. The residue was recrystallized from diethyl ether to give the title compound:

後処理

  1. temperatureto warm to ambient temperature
  2. filtrationThe slurry was filtered
  3. washthe solids were rinsed with THF
  4. temperatureThe filtrate was cooled to -10° C.
  5. customsparged with NH3 (gas) for 0.5 h
  6. temperatureto warm to 20° C.
  7. stirringstir for 15 h
  8. filtrationThe slurry was filtered
  9. additionthe filtrate was diluted with ethyl acetate
  10. washwashed with saturated NaHCO3 (3X)
  11. dry with materialThe organic phase was dried over MgSO4
  12. filtrationfiltered
  13. concentrationconcentrated in vacuo
  14. customto give a residue
  15. customThe residue was recrystallized from diethyl ether

出典と根拠

ORDレコード
ord-468f8747b02744dbb80f99592a09fdcb
出典データセット
uspto-grants-1997_06
特許番号
US05635510

反応ノート

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