(2R,4R)-4-Azido-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester → tert-butyl (2R,4R)-4-amino-2-(hydroxymethyl)pyrrolidine-1-carboxylate

HRID 244350ノート

反応式

HRID 244350 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([N:13]=[N+]=[N-])[CH2:10][C@@H:9]1[CH2:16][OH:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd].CO>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11]([NH2:13])[CH2:10][C@@H:9]1[CH2:16][OH:17])=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 2

HCID 58564434(2R,4R)-4-Azido-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl esterHCID 178418361HCID 178418361、化合物

生成物 1

HCID 45072438tert-butyl (2R,4R)-4-amino-2-(hydroxymethyl)pyrrolidine-1-carboxylate収率 98.4%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 887Methanol溶媒

実験手順

Hydrogenate a mixture of (2R,4R)-4-azido-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (225 g, 0.93 mol) and 10% palladium on carbon (22.5 g, pre-wetted with toluene) in methanol (2.3 L) at 15 psi of hydrogen at room temperature for 16 h. Filter off the catalyst and concentrate the filtrate to obtain the title compound as an oil (198 g, 92%). 1H NMR (400 MHz, DMSO-d6) δ 1.38 (s, 9H), 1.58 (m, 1H), 2.16 (m, 1H), 2.95 (m, 1H), 3.20-3.58 (m, 6H), 3.61 (m, 1H), 3.65 (br s, 1H).

後処理

  1. filtrationFilter off the catalyst
  2. concentrationconcentrate the filtrate

出典と根拠

ORDレコード
ord-7fb19b96761747ba93f21083070bb514
出典データセット
uspto-grants-2014_02
特許番号
US08658638B2

反応ノート

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