Acetic Acid → 1,1-Dimethylethyl 2-((4-(methoxycarbonyl)phenylmethylamino)methyl)-1-piperidinecarboxylate

HRID 1046299

反応式

HRID 1046299 の反応式
[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][NH2:15])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH:16]([C:18]1[CH:27]=[CH:26][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=1)=O.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.O>[CH3:25][O:24][C:22]([C:21]1[CH:26]=[CH:27][C:18]([CH2:16][NH:15][CH2:14][CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][N:8]2[C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])=[CH:19][CH:20]=1)=[O:23]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 15294Methyl 4-FormylbenzoateHCID 2756482tert-Butyl 2-(aminomethyl)piperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

生成物 1

HCID 684891571,1-Dimethylethyl 2-((4-(methoxycarbonyl)phenylmethylamino)methyl)-1-piperidinecarboxylate収率 96.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 63651,1-Dichloroethane溶媒

実験手順

A solution of 1-Boc-2-aminomethylpiperidine (429 mg, 2 mmol) and methyl 4-formylbenzoate (329 mg, 2 mmol) in dichloroethane (10 mL) was stirred as acetic acid (180 mg, 3 mmol) and sodium triacetoxyborohydride (487 mg, 2.3 mmol) were added sequentially. The reaction was stirred at ambient temperature for 17 hours. The reaction was poured into water and extracted with methylene chloride (2×). The organic phase was dried over sodium sulfate, filtered, and concentrated. Purification on silica gel using a gradient of ethyl acetate in hexane gave 0.7 g of 1,1-dimethylethyl 2-((4-(methoxycarbonyl)phenylmethylamino)methyl)-1-piperidinecarboxylate.

後処理

  1. additionwere added sequentially
  2. extractionextracted with methylene chloride (2×)
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification on silica gel using a gradient of ethyl acetate in hexane

出典と根拠

ORDレコード
ord-a4af34579fff4ba78e1753f5c4d0274e
出典データセット
uspto-grants-2013_10
特許番号
US08569303B2

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