8-Methyl-8-azabicyclo(3.2.1)octan-3-ol → HCID 67607346, compound

HRID 1619536Notes

Reaction equation

HRID 1619536 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=NC1CCCCC1)=NC1CCCCC1.N1(O)C2C=CC=CC=2N=N1.[CH3:44][N:45]1[CH:50]2[CH2:51][CH2:52][CH:46]1[CH2:47][CH:48](O)[CH2:49]2>C1COCC1>[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:10]([O:12][CH:48]1[CH2:49][CH:50]2[N:45]([CH3:44])[CH:46]([CH2:52][CH2:51]2)[CH2:47]1)=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 84248-Methyl-8-azabicyclo(3.2.1)octan-3-olHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 5718052-(((Tert-butoxy)carbonyl)amino)-2-phenylacetic acid

Product 1

HCID 67607346HCID 67607346, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(tert-butoxycarbonylamino)-2-phenylacetic acid (400 mg, 1.59 mmol) in THF (20 ml), were added N,N′-methanediylidenedicyclohexanamine (394 mg, 1.91 mmol), 1H-benzo[d][1,2,3]triazol-1-ol (258 mg, 1.91 mmol) and 8-methyl-8-azabicyclo[3.2.1]octan-3-ol (270 mg, 1.91 mmol). The reaction was stirred at RT for 15 hours, and then the solvent was evaporated. The residue was taken up with DCM, the insoluble was filtered off, and the clear solution was washed twice with aq. Na2CO3 and brine, dried over Na2SO4 and evaporated to give 8-methyl-8-azabicyclo[3.2.1]octan-3-yl 2-(tert-butoxycarbonylamino)-2-phenylacetate (460 mg; 77% yield). The product was used in the next step without any further purification.

Workup

  1. customthe solvent was evaporated
  2. filtrationthe insoluble was filtered off
  3. washthe clear solution was washed twice with aq. Na2CO3 and brine
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-b483db5e436b4557a478d8e40e92f843
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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