Sodium borohydride → benzyl 4-((1R,2S)-2-{2-[(5-amino-3-methylpyridin-2-yl)oxy]ethyl}cyclopropyl)piperidine-1-carboxylate

HRID 1850750ノート

反応式

HRID 1850750 の反応式
[BH4-].[Na+].[CH3:3][C:4]1[C:5]([O:13][CH2:14][CH2:15][C@@H:16]2[CH2:18][C@@H:17]2[CH:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:26])[CH2:21][CH2:20]2)=[N:6][CH:7]=[C:8]([N+:10]([O-])=O)[CH:9]=1>CO.C(Cl)Cl.Cl[Ni]Cl>[NH2:10][C:8]1[CH:9]=[C:4]([CH3:3])[C:5]([O:13][CH2:14][CH2:15][C@@H:16]2[CH2:18][C@@H:17]2[CH:19]2[CH2:24][CH2:23][N:22]([C:25]([O:27][CH2:28][C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)=[O:26])[CH2:21][CH2:20]2)=[N:6][CH:7]=1

参加物

6

反応物 2

HCID 4311764Sodium borohydride2 回HCID 70819067Benzyl 4-((1R,2S)-2-{2-[(3-methyl-5-nitropyridin-2-yl)oxy]ethyl}cyclopropyl)piperidine-1-carboxylate

生成物 1

HCID 70856037benzyl 4-((1R,2S)-2-{2-[(5-amino-3-methylpyridin-2-yl)oxy]ethyl}cyclopropyl)piperidine-1-carboxylate

試薬・触媒・溶媒 3

HCID 24385Nickel Dichloride触媒HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To the solution of NiCl2 (Nickel (II) Chloride-hexahydrate, 1.03 g, 4.32 mmol) in 40 ml of methanol was added 150 mg of NaBH4 (it turned dark) at RT and the mixture stirred 5 minutes. Benzyl 4-((1R,2S)-2-{-[(3-methyl-5-nitropyridin-2-yl)oxy]ethyl}cyclopropyl)piperidine-1-carboxylate (1.90 g, 4.32 mmol) in 15 ml of DCM was added followed by the addition of another 116 mg of NaBH4 in 3 portions. The resulting mixture was then stirred for 40 minutes. The reaction was then diluted with DCM and filtered through a celite and silica gel pad. The filtrate was concentrated in vacuo and the residue was partitioned between saturated NaHCO3 aqueous solution and DCM. The organics were separated, dried over sodium sulfate, filtered and the filtrate concentrated under reduced pressure to afford the title compound as a crude product which was used for the next step. LC/MS (m/z): 410 (M+H)+.

後処理

  1. stirringThe resulting mixture was then stirred for 40 minutes
  2. filtrationfiltered through a celite and silica gel pad
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was partitioned between saturated NaHCO3 aqueous solution and DCM
  5. customThe organics were separated
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate concentrated under reduced pressure

出典と根拠

ORDレコード
ord-66876de15f81430bbdd47809bc3c0249
出典データセット
uspto-grants-2015_02
特許番号
US08957062B2

反応ノート

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