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

HRID 1466015Notes

Reaction equation

HRID 1466015 reaction equation
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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

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]+.

Workup

  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

Sources & evidence

ORD record
ord-0c62d7bb25aa4a75838b4dd9807c69cb
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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