tert-Butyl piperazine-1-carboxylate → HCID 67513971, compound

HRID 1519639Notes

Reaction equation

HRID 1519639 reaction equation
[F:1][CH:2]([F:15])[O:3][C:4]1[CH:11]=[C:10]([CH2:12][CH:13]=O)[CH:9]=[CH:8][C:5]=1[C:6]#[N:7].[C:16]([N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[C:19]([O:18][C:16]([N:23]1[CH2:28][CH2:27][N:26]([CH2:13][CH2:12][C:10]2[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[C:4]([O:3][CH:2]([F:15])[F:1])[CH:11]=2)[CH2:25][CH2:24]1)=[O:17])([CH3:22])([CH3:20])[CH3:21]

Participants

5

Reactant 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 86694483HCID 86694483, compound

Product 1

HCID 67513971HCID 67513971, compoundYield 27.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of crude compound 2-(difluoromethoxy)-4-(2-oxoethyl)benzonitrile (100 mg, 0.48 mmol), N-Boc Piperazine (100 mg, 0.54 mmol) and NaBH(OAc)3 (0.4 g, 2 mmol) in 20 mL of anhydrous DCM was stirred at ambient temperature overnight. The reaction mixture was added 50 mL of DCM, washed with brine. The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was purified with prep-TLC to afford tert-butyl-4-{2-[4-cyano-3-(difluoromethoxy)phenyl]ethyl}piperazine-1-carboxylate (50 mg, 27% yield). The material was further treated with TFA to remove the Boc group. The crude product was used directly in the next step. MS: m/e 282 (M+1)+.

Workup

  1. washwashed with brine
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified with prep-TLC

Sources & evidence

ORD record
ord-c09b8c0053624f81a415c033ce22ac5e
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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