Acetic Acid → HCID 86713811, compound

HRID 521862Notes

Reaction equation

HRID 521862 reaction equation
[CH3:1][N:2]1[C:6]([CH:7]2[CH2:13][O:12][CH2:11][C:10](=O)[CH2:9][CH2:8]2)=[C:5]([N+:15]([O-:17])=[O:16])[CH:4]=[N:3]1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:24].[Na+].C(O)(=O)C.[C:31]([O:35][C:36]([O:38]C(OC(C)(C)C)=O)=O)([CH3:34])([CH3:33])[CH3:32].CCN(C(C)C)C(C)C>CO>[CH3:1][N:2]1[C:6]([CH:7]2[CH2:13][O:12][CH2:11][CH:10]([NH:24][C:36](=[O:38])[O:35][C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:9][CH2:8]2)=[C:5]([N+:15]([O-:17])=[O:16])[CH:4]=[N:3]1

Participants

8

Reactant 6

HCID 176Acetic AcidHCID 81531DiisopropylethylamineHCID 90495Di-tert-butyl dicarbonateHCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 86713810HCID 86713810, compound

Product 1

HCID 86713811HCID 86713811, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6-(2-Methyl-4-nitro-pyrazol-3-yl)oxepan-3-one (53 mg, 0.23 mmol), ammonium acetate (219 mg, 2.76 mmol), sodium cyanoborohydride (38 mg, 0.57 mmol) and a few pettets of 4A molecular seives were dissolved in methanol (2 mL). Acetic acid (35 mg, 0.57 mmol) was added and the mixture was stirred at RT under N2 atmosphere for three days. The reaction was quenched with sat. sodium bicarbonate and extracted with DCM (3×). Combined organic layers were dried (MgSO4) and the solvent removed under reduced pressure. The residue was dissolved in DCM (5 mL) and di-tert-butyl-dicarbonate (63 mg, 0.69 mmol) and DIPEA (0.067 mL, 0.38 mmol) were added. The mixture was stirred at room temperature overnight and then purified via silica gel chromatography (0-100% EtOAc/heptane) to afford tert-butyl N-[6-(2-methyl-4-nitro-pyrazol-3-yl)oxepan-3-yl]carbamate (53 mg, 81%).

Workup

  1. customThe reaction was quenched with sat. sodium bicarbonate
  2. extractionextracted with DCM (3×)
  3. dry with materialCombined organic layers were dried (MgSO4)
  4. customthe solvent removed under reduced pressure
  5. dissolutionThe residue was dissolved in DCM (5 mL)
  6. stirringThe mixture was stirred at room temperature overnight
  7. custompurified via silica gel chromatography (0-100% EtOAc/heptane)

Sources & evidence

ORD record
ord-acf79389fc9d492899f794517fa54e31
Source dataset
uspto-grants-2016_05
Patent number
US09328106B2

Reaction notes

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