tert-Butyl piperazine-1-carboxylate → HCID 67517481, compound

HRID 2173122Notes

Reaction equation

HRID 2173122 reaction equation
[I:1][C:2]1[C:10]2[CH2:9][O:8][C:7](=[O:11])[C:6]=2[CH:5]=[CH:4][C:3]=1[CH2:12][CH:13]=O.[C:15]([N:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[C:18]([O:17][C:15]([N:22]1[CH2:27][CH2:26][N:25]([CH2:13][CH2:12][C:3]2[CH:4]=[CH:5][C:6]3[C:7](=[O:11])[O:8][CH2:9][C:10]=3[C:2]=2[I:1])[CH2:24][CH2:23]1)=[O:16])([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 3

HCID 143452tert-Butyl piperazine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 87429801HCID 87429801, compound

Product 1

HCID 67517481HCID 67517481, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

The crude (4-iodo-1-oxo-1,3-dihydro-2-benzofuran-5-yl)acetaldehyde (1.2 g) was dissolved in DCM (40 mL). Boc-piperazine (1.1 g, 5.9 mmol) was added into the solution, followed by addition of sodium triacetoxyborohydride (4.2 g, 20 mmol). The reaction was allowed to stir at RT overnight. The reaction was diluted with DCM, washed with sodium bicarbonate and brine, dried over MgSO4, and purified by silica gel chromatography to furnish tert-butyl-4-[2-(4-iodo-1-oxo-1,3-dihydro-2-benzofuran-5-yl)ethyl]piperazine-1-carboxylate. LC-MS (IE, m/z): 473 [M+1]+.

Workup

  1. washwashed with sodium bicarbonate and brine
  2. dry with materialdried over MgSO4
  3. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-b953d833c59f4dfa80504f9138897e7a
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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