Hydrochloric Acid → Phenylmethyl 3-amino-1-piperidinecarboxylate

HRID 919588ノート

反応式

HRID 919588 の反応式
C(OC([NH:8][CH:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:10]1)=O)(C)(C)C.Cl>O1CCOCC1>[NH2:8][CH:9]1[CH2:14][CH2:13][CH2:12][N:11]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH2:10]1

参加物

4

反応物 2

HCID 313Hydrochloric AcidHCID 22258937Benzyl 3-(tert-butoxycarbonylamino)piperidine-1-carboxylate

生成物 1

HCID 2756612Phenylmethyl 3-amino-1-piperidinecarboxylate収率 99.9%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

Benzyl 3-(tert-butoxycarbonylamino)piperidine-1-carboxylate (1 g, 2.99 mmol) was treated with Dioxane.HCl (30 mL) at 0° C. The reaction mixture was stirred at rt for 1 h. After completion of the reaction mixture, the solvent was removed under vacuo and the residue was dissolved in H2O (10 mL). The aqueous layer was treated with solid Na2CO3 until effervescence ceases and the solution was extracted with EtOAc (3×25 mL). The combined organic layer was dried over Na2SO4, concentrated to yield titled intermediate (700 mg, 92%), which was used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6): δ 7.41-7.25 (m, 5H), 5.08 (s, 2H), 3.95-3.78 (m, 2H), 3.22 (bs, 2H), 2.82-2.75 (m, 1H), 2.61-2.45 (m, 2H), 1.82-1.78 (m, 1H), 1.69-1.59 (m, 1H), 1.40-1.33 (m, 1H), 1.22-1.10 (m, 1H). ES-MS: m/z [M+1]=235.

後処理

  1. customat 0° C
  2. customAfter completion of the reaction mixture, the solvent was removed under vacuo
  3. dissolutionthe residue was dissolved in H2O (10 mL)
  4. additionThe aqueous layer was treated with solid Na2CO3 until effervescence ceases
  5. extractionthe solution was extracted with EtOAc (3×25 mL)
  6. dry with materialThe combined organic layer was dried over Na2SO4
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-ea8788a0e9e44f5eb57ea89b32e3ee64
出典データセット
uspto-grants-2016_03
特許番号
US09273028B2

反応ノート

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