Ethanol → 4-(3-Quinuclidinyl)piperazine-1-carboxylic acid, 1,1-dimethylethyl ester

HRID 494011ノート

反応式

HRID 494011 の反応式
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH2:3][C:2]2=O.[C:10]([O:14][C:15]([N:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)=[O:16])([CH3:13])([CH3:12])[CH3:11].C(O)C.C([BH3-])#N.[Na+]>CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-].O>[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[CH:3]([N:20]1[CH2:19][CH2:18][N:17]([C:15]([O:14][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:16])[CH2:22][CH2:21]1)[CH2:2]2

参加物

7

反応物 4

HCID 702EthanolHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5661192-QuinuclidoneHCID 5003444Sodium cyanoborohydride

生成物 1

HCID 910215394-(3-Quinuclidinyl)piperazine-1-carboxylic acid, 1,1-dimethylethyl ester収率 42%

試薬・触媒・溶媒 2

HCID 11026Titanium isopropoxide触媒HCID 962Water溶媒

実験手順

1 g (8 mM) of quinuclidinone, 1.63 g (8.75 mM) of 1-piperazinecarboxylic acid t-butyl ester (1-Boc-piperazine) and 2.71 ml (9.1 mM) of titanium isopropoxide are mixed and this mixture is kept under agitation for 1 hour. 5 ml of ethanol and then 460 mg (7.3 mM) of sodium cyanoborohydride are then added, and this mixture is agitated for 24 hours at ambient temperature. 25 ml of water are added and agitation is carried out for 15 minutes. The precipitate formed is separated off by filtration and the filtrate is concentrated under reduced pressure. The residue is purified by NH2 silica gel chromatography in eluting with the aid of a toluene/isopropanol mixture (95/5; v/v). 1 g of the compound sought after are thus obtained as a white solid (yield=42%).

後処理

  1. waitagitation is carried out for 15 minutes
  2. customThe precipitate formed
  3. customis separated off by filtration
  4. concentrationthe filtrate is concentrated under reduced pressure
  5. customThe residue is purified by NH2 silica gel chromatography
  6. washin eluting with the aid of a toluene/isopropanol mixture (95/5; v/v)

出典と根拠

ORDレコード
ord-e5a115c959e44ff1b082c015be20cf54
出典データセット
uspto-grants-2009_05
特許番号
US07538111B2

反応ノート

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