Sodium Bicarbonate → HCID 21927829, compound

HRID 1243525Notes

Reaction equation

HRID 1243525 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][N:11]([CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH2:10][CH2:9]1)[C:2]1[CH:7]=CC=CC=1.O=CCCC[NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCl.O>[C:29]([O:28][C:27]([NH:26][CH2:7][CH2:2][CH2:1][N:8]1[CH2:9][CH2:10][N:11]([CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])[CH2:12][CH2:13]1)=[O:33])([CH3:32])([CH3:31])[CH3:30]

Participants

7

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 15147569HCID 15147569, compoundHCID 15534785tert-Butyl (4-oxobutyl)carbamate

Product 1

HCID 21927829HCID 21927829, compoundYield 78.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 4-(4-benzylpiperazin-1-yl)butanoate (500 mg, 2.68 mmoles) in dichloromethane (5 mL) was added tert-butyl 4-oxobutyl-carbamate (505 mg, 2.68 mmoles) and sodium triacetoxyborohydride (900 mg, 1.5 eq) and stirred 20 h. To the reaction mixture water was added followed by 1M aqueous sodium bicarbonate solution. The solution was extracted with ethyl acetate. The organics were evaporated to afford methyl 4-(4-{3-[(tert-butoxycarbonyl)amino]propyl}-piperazin-1-yl)butanoate (0.72 g, 75%). MS (ESI+) for m/z 358 (M+H)+.

Workup

  1. extractionThe solution was extracted with ethyl acetate
  2. customThe organics were evaporated

Sources & evidence

ORD record
ord-76e7929fe3d34e70bd47477d7bcfbc3e
Source dataset
uspto-grants-2006_10
Patent number
US07119098B2

Reaction notes

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