Ozone → tert-Butyl 4-(6-cyano-1,2,3,4-tetrahydronaphthalen-2-yl)-3-oxopiperazine-1-carboxylate

HRID 1466015ノート

反応式

HRID 1466015 の反応式
O=[O+][O-].[CH2:4]([N:7]([CH2:15][C:16]([O:18]C)=O)[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH:5]=C.[NH2:20][CH:21]1[CH2:30][CH2:29][C:28]2[CH:27]=[C:26]([C:31]#[N:32])[CH:25]=[CH:24][C:23]=2[CH2:22]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[C:31]([C:26]1[CH:27]=[C:28]2[C:23](=[CH:24][CH:25]=1)[CH2:22][CH:21]([N:20]1[CH2:5][CH2:4][N:7]([C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9])[CH2:15][C:16]1=[O:18])[CH2:30][CH2:29]2)#[N:32]

参加物

6

反応物 4

HCID 24823OzoneHCID 5049666Sodium triacetoxyborohydrideHCID 22243128N-Boc-allylglycine methyl esterHCID 513583406-Amino-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

生成物 1

HCID 131732668tert-Butyl 4-(6-cyano-1,2,3,4-tetrahydronaphthalen-2-yl)-3-oxopiperazine-1-carboxylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

Ozone was bubbled into a solution of methyl [allyl(tert-butoxycarbonyl)amino]acetate (3.6 g, 16 mmol) in DCM at −78° C. until it turned pale blue. Nitrogen was then bubbled into the solution to remove excess ozone. When the blue color was gone, 6-amino-5,6,7,8-tetrahydronaphthalene-2-carbonitrile (2.7 g, 16 mmol) and sodium triacetoxyborohydride (20 g, 95 mmol) was added to the reaction, and the mixture was allowed to warm to RT. The reaction was diluted with DCM, washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate, and purified by preparative TLC to afford the title compound. LC-MS (IE, m/z): 256 [M−Boc+1]+.

後処理

  1. customNitrogen was then bubbled into the solution
  2. customto remove excess ozone
  3. washwashed with aqueous sodium bicarbonate and brine
  4. dry with materialdried over magnesium sulfate
  5. custompurified by preparative TLC

出典と根拠

ORDレコード
ord-0c62d7bb25aa4a75838b4dd9807c69cb
出典データセット
uspto-grants-2015_04
特許番号
US08999990B2

反応ノート

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