Trifluoroacetic acid → tert-Butyl piperazine-1-carboxylate

HRID 2167350Notes

Reaction equation

HRID 2167350 reaction equation
[CH3:1][C:2]1[CH:7]=CC(S([O-])(=O)=O)=C[CH:3]=1.C1[CH:17]=[CH:16][NH+:15]=[CH:14][CH:13]=1.[Si](C#N)(C)(C)C.[Al](C#[N:30])(CC)CC.[C:31]([OH:37])(C(F)(F)F)=[O:32].S(Cl)(Cl)(=O)=O>[Zn+2].[I-].[I-].C(Cl)Cl.CCN(CC)CC.C1(C)C=CC=CC=1.CCOCC.CO.CC#N.O>[N:15]1([C:31]([O:37][C:2]([CH3:1])([CH3:3])[CH3:7])=[O:32])[CH2:14][CH2:13][NH:30][CH2:17][CH2:16]1

Participants

13

Reactant 5

HCID 6422Trifluoroacetic acidHCID 24648Sulfuryl chlorideHCID 82115Trimethylsilyl cyanideHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 16683962(cyano-C)diethylaluminium

Product 1

HCID 143452tert-Butyl piperazine-1-carboxylate

Reagents, catalysts & solvents 7

HCID 9883512zinc(II)iodideCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolventHCID 21864698Diethyl ether methanolSolvent

Procedure

Conditions: K1) Na2S2O5 or PPTS, H2O, CH3CN; K2) TMSCN, ZnI2, Et2O/CH3OH; K3) Et2AlCN, Ti(i-PrO)4, toluene; L) TFA, CH2Cl2; M) sulfonyl chloride, Et3N, CH2Cl2

Sources & evidence

ORD record
ord-a722dfb062cb4155b2dc5bbc40b0f71d
Source dataset
uspto-grants-2015_06
Patent number
US09045445B2

Reaction notes

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