Tert-Butyl nitrite → HCID 59542572, compound

HRID 1809055Notes

Reaction equation

HRID 1809055 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[S:18][C:19](N)=[C:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:21]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N(OC(C)(C)C)=O.[Cl-].[NH4+]>[Cu](Cl)Cl>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17]2[S:18][CH:19]=[C:20]([C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH:21]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10906Tert-Butyl nitriteHCID 25517Ammonium ChlorideHCID 59542488HCID 59542488, compound

Product 1

HCID 59542572HCID 59542572, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 24014Cupric ChlorideCatalyst

Procedure

4-(5-Amino-4-ethoxycarbonyl-thiophen-2-yl)-piperidine-1-carboxylic acid benzyl ester (1.46 g, 3.76 mmol) was added to t-butyl nitrite (5.64 mmol) and copper(II)chloride (3.76 mmol) in IMS (40 mL). The reaction was stirred for 1.5 hours then saturated aqueous ammonium chloride (7 mL) was added and the resulting mixture stirred for a further 15 minutes. The solvent was removed under vacuum and product partitioned between ethyl acetate and water. The organic layer was dried over magnesium sulphate, filtered and the solvent removed to give the title compound (1.17 g). LCMS m/z 374 [M+H]+ RT=4.18 min (Analytical Method 4).

Workup

  1. stirringthe resulting mixture stirred for a further 15 minutes
  2. customThe solvent was removed under vacuum and product
  3. custompartitioned between ethyl acetate and water
  4. dry with materialThe organic layer was dried over magnesium sulphate
  5. filtrationfiltered
  6. customthe solvent removed

Sources & evidence

ORD record
ord-33f513fe5ecc4e9e861ff8196b6b39f7
Source dataset
uspto-grants-2013_01
Patent number
US08362008B2

Reaction notes

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