Triethylamine → HCID 86689215, compound

HRID 594953Notes

Reaction equation

HRID 594953 reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[C:18]([O:22][C:23]([N:25]1[CH:30]2[CH2:31][CH2:32][CH:26]1[CH:27](C(O)=O)[CH2:28][CH2:29]2)=[O:24])([CH3:21])([CH3:20])[CH3:19].C([N:38]([CH2:41]C)CC)C.CC[O:45]C(C)=O>C1(C)C=CC=CC=1>[N:38]([CH:27]1[CH2:28][CH2:29][CH:30]2[N:25]([C:23]([O:22][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:24])[CH:26]1[CH2:32][CH2:31]2)=[C:41]=[O:45]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 199401P,P-Diphenylphosphinic azideHCID 668014908-Azabicyclo[3.2.1]octane-2,8-dicarboxylic acid, 8-(1,1-dimethylethyl) ester

Product 1

HCID 86689215HCID 86689215, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

Diphenylphosphoryl azide (890 mg, 3.23 mmol) was added into a solution of 8-(tert-butoxycarbonyl)-8-azabicyclo[3.2.1]octane-2-carboxylic acid (0.75 g, 2.94 mmol) and triethylamine (595 mg, 5.88 mmol) in toluene (10 ml). The reaction solution was heated at 100° C. for 5 h. EtOAc (50 ml) was added and the resulting solution was washed with water (10 ml). The organic layer was separated, and dried over sodium sulfate. The solution was filtered, concentrated, and used in the next step without further purification.

Workup

  1. washthe resulting solution was washed with water (10 ml)
  2. customThe organic layer was separated
  3. dry with materialdried over sodium sulfate
  4. filtrationThe solution was filtered
  5. concentrationconcentrated
  6. customused in the next step without further purification

Sources & evidence

ORD record
ord-5fe20e6063fa4731b44d5314ef74d432
Source dataset
uspto-grants-2016_01
Patent number
US09242981B2

Reaction notes

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