tert-Butyl piperazine-1-carboxylate → HCID 86693013, compound

HRID 2173294Notes

Reaction equation

HRID 2173294 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[Br:14][C:15]1[C:23]2[O:22][CH:21]=[C:20]([CH:24]=O)[C:19]=2[CH:18]=[CH:17][CH:16]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CCOC(C)=O>[Br:14][C:15]1[C:23]2[O:22][CH:21]=[C:20]([CH2:24][N:11]3[CH2:10][CH2:9][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[CH2:13][CH2:12]3)[C:19]=2[CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 77230761HCID 77230761, compound

Product 1

HCID 86693013HCID 86693013, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a flask charged with Boc-piperazine (130 mg, 0.70 mmol) and 7-bromo-1-benzofuran-3-carbaldehyde (141 mg, 0.63 mmol) was added NaBH(OAc)3 (761 mg, 2.80 mmol). The mixture was stirred at room temperture for 12 hours. Then the reaction was diluted with EtOAc (50 mL), washed with brine (15 mL), dried over Na2SO4 and concentrated. The residue was purified with prep-TLC to obtain the pure product tert-butyl 4-[(7-bromo-1-benzofuran-3-yl)methyl]piperazine-1-carboxylate.

Workup

  1. washwashed with brine (15 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified with prep-TLC

Sources & evidence

ORD record
ord-db6006bbb3b441c59a56eacc0ef75b11
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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