Dimethylamine → (1S-trans)-[3-(N,N-Dimethylamino)cyclopentyl]carbamic acid 1,1-dimethylethyl ester

HRID 1420311ノート

反応式

HRID 1420311 の反応式
[CH3:1][C:2]([O:5][C:6](=[O:18])[NH:7][C@H:8]1[CH2:12][CH2:11][C@@H:10](OS(C)(=O)=O)[CH2:9]1)([CH3:4])[CH3:3].[CH3:19][NH:20][CH3:21]>O>[CH3:1][C:2]([O:5][C:6](=[O:18])[NH:7][C@H:8]1[CH2:12][CH2:11][C@H:10]([N:20]([CH3:21])[CH3:19])[CH2:9]1)([CH3:4])[CH3:3]

参加物

4

反応物 2

HCID 674DimethylamineHCID 86608906(1R,3S)-3-[(tert-butoxycarbonyl)amino]cyclopentyl methanesulfonate

生成物 1

HCID 67640823(1S-trans)-[3-(N,N-Dimethylamino)cyclopentyl]carbamic acid 1,1-dimethylethyl ester

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

(1S-cis)-[3-[(Methylsulphonyl)oxy]cyclopentyl]carbamic acid 1,1-dimethylethyl ester (1.452 g, 5.20 mmol) in a solution of dimethylamine (33% in ethanol, 25 ml) was heated at reflux for 3.75 h, then allowed to cool. The solution was diluted with water (100 ml) and extracted with ethyl acetate(3×100 ml). The total organic solution was dried (Na2SO4) and evaporated to a yellow gum. This was purified on silica, eluting with dichloromethane:ethanol:0.88 ammonia (100:8:1) changing to (30:8:1) to give a brown film (0.988 g, 83%). A portion of this was evaporated from a solution in isopropyl ether to give the title compound (0.139 g) as a brown solid, m.p. 65°-67° C., [α]D -40.35°(CHCl3 c=0.57%).

後処理

  1. temperatureat reflux for 3.75 h
  2. temperatureto cool
  3. extractionextracted with ethyl acetate(3×100 ml)
  4. dry with materialThe total organic solution was dried (Na2SO4)
  5. customevaporated to a yellow gum
  6. customThis was purified on silica
  7. washeluting with dichloromethane
  8. customto give a brown film (0.988 g, 83%)
  9. customA portion of this was evaporated from a solution in isopropyl ether

出典と根拠

ORDレコード
ord-719de83aabb64c0a994baa7fe55506e5
出典データセット
uspto-grants-1999_03
特許番号
US05889178

反応ノート

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