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

HRID 1466015노트

반응식

HRID 1466015 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-0c62d7bb25aa4a75838b4dd9807c69cb
출처 데이터셋
uspto-grants-2015_04
특허 번호
US08999990B2

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