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Potassium bisulfate → benzyl N-[3-(2-aminoethyl)pyrrolidine-1-carboximidoyl]carbamate

HRID 869
ノート
印刷プレビュー

反応式

HRID 869 の反応式
C(OC([NH:8][CH2:9][CH2:10][CH:11]1[CH2:15][CH2:14][NH:13][CH2:12]1)=O)(C)(C)C.[CH2:16]([O:23][C:24]([NH:26][C:27](=[NH:30])SC)=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.OS([O-])(=O)=O.[K+]>C1(C)C=CC=CC=1>[CH2:16]([O:23][C:24]([NH:26][C:27]([N:13]1[CH2:14][CH2:15][CH:11]([CH2:10][CH2:9][NH2:8])[CH2:12]1)=[NH:30])=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 516920Potassium bisulfateHCID 21955469tert-butyl N-[2-(pyrrolidin-3-yl)ethyl]carbamateHCID 140362141Benzyl [amino(methylsulfanyl)methylene]carbamate

生成物 1

HCID 140379083benzyl N-[3-(2-aminoethyl)pyrrolidine-1-carboximidoyl]carbamate収率 67.5%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

2.18 g (0.0102 mole) (3RS)-3-(N-tert-butyloxycarbonylaminoethyl) pyrrolidine and 2.81 g (0.0125 mole) N-benzyloxycarbonyl-S-methylisothiourea was dissolved in 30 ml toluene and heated to 60°-70° C. for eight hours followed by stirring at room temperature for one day. 0.3M KHSO4 -solution was added and the water layer was washed with a mixture of the toluene and ethyl acetate and left for 2 days under which time the Boc group was removed. The acidic water phase was made alkaline and extracted four times with CH2 Cl2. The combined organic layer was dried (Na2SO4), filtered and evaporated to yield 2.0 g (51%) of the title compound.

後処理

  1. temperatureheated to 60°-70° C. for eight hours
  2. washthe water layer was washed with a mixture of the toluene and ethyl acetate
  3. waitleft for 2 days under which time the Boc group
  4. customwas removed
  5. extractionextracted four times with CH2 Cl2
  6. dry with materialThe combined organic layer was dried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated

出典と根拠

ORDレコード
ord-d42f48a7d3fc473aba6c5139093935b5
出典データセット
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05723444

反応ノート

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