Acetic Acid → HCID 59186703, compound

HRID 731549Notes

Reaction equation

HRID 731549 reaction equation
[CH3:1][O:2][C:3]1([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[CH2:8][CH2:7][C:6](=O)[CH2:5][CH2:4]1.[C:18]([O:22][C:23]([N:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1)=[O:24])([CH3:21])([CH3:20])[CH3:19].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.C(OCC)(=O)C>[CH3:1][O:2][C:3]1([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])[CH2:8][CH2:7][CH:6]([N:28]2[CH2:27][CH2:26][N:25]([C:23]([O:22][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:24])[CH2:30][CH2:29]2)[CH2:5][CH2:4]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 59186632HCID 59186632, compound

Product 1

HCID 59186703HCID 59186703, compoundYield 70.4%

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of EXAMPLE 15C (0.42 g, 1.80 mmol) and 1-tert-butoxycarbonylpiperazine (0.391 g, 2.10 mmol) in dichloroethane (10 mL) at room temperature was treated with acetic acid (500 μL) and sodium triacetoxyborohydride (10.89 g, 4.2 mmol), stirred overnight, diluted with ethyl acetate (300 mL), washed sequentially with 1N NaOH, water, and brine, dried (Na2SO4), filtered, and concentrated to provide the desired product (0.51 g, 70%); MS (ESI) m/e 403 (M+H)+.

Workup

  1. washwashed sequentially with 1N NaOH, water, and brine
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-866da1003a784115aea7677ca70e8941
Source dataset
uspto-grants-2009_09
Patent number
US07585858B2

Reaction notes

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