(R)-2-((2-cyano-3-nitrophenoxy)methyl)-N-(pyridin-4-ylmethyl)piperidine-1-carboxamide → (R)-2-((3-amino-2-cyanophenoxy)methyl)-N-(pyridin-4-ylmethyl)piperidine-1-carboxamide

HRID 1483970ノート

反応式

HRID 1483970 の反応式
[C:1]([C:3]1[C:26]([N+:27]([O-])=O)=[CH:25][CH:24]=[CH:23][C:4]=1[O:5][CH2:6][C@H:7]1[CH2:12][CH2:11][CH2:10][CH2:9][N:8]1[C:13]([NH:15][CH2:16][C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1)=[O:14])#[N:2]>C1COCC1.C(O)(=O)C.[Fe]>[NH2:27][C:26]1[C:3]([C:1]#[N:2])=[C:4]([CH:23]=[CH:24][CH:25]=1)[O:5][CH2:6][C@H:7]1[CH2:12][CH2:11][CH2:10][CH2:9][N:8]1[C:13]([NH:15][CH2:16][C:17]1[CH:18]=[CH:19][N:20]=[CH:21][CH:22]=1)=[O:14]

参加物

4

反応物 1

HCID 86714302(R)-2-((2-cyano-3-nitrophenoxy)methyl)-N-(pyridin-4-ylmethyl)piperidine-1-carboxamide

生成物 1

HCID 86714301(R)-2-((3-amino-2-cyanophenoxy)methyl)-N-(pyridin-4-ylmethyl)piperidine-1-carboxamide収率 40%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 23444217Acetic acid tetrahydrofuran溶媒

実験手順

To a solution of (R)-2-((2-cyano-3-nitrophenoxy)methyl)-N-(pyridin-4-ylmethyl)piperidine-1-carboxamide (Example 27c, 365 mg, 0.98 mmol) in THF/acetic acid (20 mL, 1:1), was added iron powder (164 mg, 2.94 mmol). The reaction was heated to reflux over 15 min under nitrogen, and stirred at reflux for 30 min. Upon completion, the reaction was cooled to room temperature, concentrated, diluted with ethyl acetate and successively washed a saturated solution of NaHCO3, dried over Na2SO4, filtered, concentrated and flash chromatographed (0-10% methanol in dichloromethane) to provide the desired product (141 mg, 40%). MS=366 (MH+).

後処理

  1. temperatureThe reaction was heated
  2. temperatureto reflux over 15 min under nitrogen
  3. temperatureat reflux for 30 min
  4. concentrationconcentrated
  5. additiondiluted with ethyl acetate
  6. washsuccessively washed a saturated solution of NaHCO3
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customflash chromatographed (0-10% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-a01048fd571741228c4c598c8ef824e4
出典データセット
uspto-grants-2016_08
特許番号
US09420814B2

反応ノート

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