tert-Butyl piperazine-1-carboxylate → Tert-butyl 4-[2-(4-cyano-3-fluorophenyl)ethyl]piperazine-1-carboxylate

HRID 1519629Notes

Reaction equation

HRID 1519629 reaction equation
[F:1][C:2]1[CH:9]=[C:8]([CH2:10][CH:11]=O)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[C:13]([N:20]1[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]1)([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[C:4]([C:3]1[CH:6]=[CH:7][C:8]([CH2:10][CH2:11][N:23]2[CH2:22][CH2:21][N:20]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:25][CH2:24]2)=[CH:9][C:2]=1[F:1])#[N:5]

Participants

5

Reactant 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 866944782-Fluoro-4-(2-oxoethyl)benzonitrile

Product 1

HCID 67513450Tert-butyl 4-[2-(4-cyano-3-fluorophenyl)ethyl]piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of crude 2-fluoro-4-(2-oxoethyl)benzonitrile (900 mg, 5.5 mmol) in 20 mL of DCM was added N-Boc Piperazine (1.0 g, 5.5 mmol) and NaBH(OAc)3 (4.7 g, 22 mmol), the mixture was stirred at room temperature overnight. The reaction was diluted with DCM, and washed with brine, the organic layer was dried over anhydrous Na2SO4 and concentrated. The residue was purified by preparative TLC to give tert-butyl 4-[2-(4-cyano-3-fluorophenyl)ethyl]piperazine-1-carboxylate.

Workup

  1. washwashed with brine
  2. dry with materialthe organic layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by preparative TLC

Sources & evidence

ORD record
ord-da42928356164b09b2350c7a430c81d6
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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