tert-Butanol → tert-Butyl (3-benzyl-3-azabicyclo[3.1.0]hexan-6-yl)carbamate

HRID 54712Notes

Reaction equation

HRID 54712 reaction equation
Cl.[CH2:2]([N:9]1[CH2:14][CH:13]2[CH:11]([CH:12]2C(O)=O)[CH2:10]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([N:20]([CH2:23]C)CC)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:32])=CC=1.[C:42]([OH:46])([CH3:45])([CH3:44])[CH3:43]>O.C1(C)C=CC=CC=1>[CH2:2]([N:9]1[CH2:10][CH:11]2[CH:13]([CH:12]2[NH:20][C:23]([O:46][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:32])[CH2:14]1)[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 677254043-Benzyl-3-azabicyclo[3.1.0]hexane-6-carboxylic acid hydrochloride

Product 1

HCID 9860737tert-Butyl (3-benzyl-3-azabicyclo[3.1.0]hexan-6-yl)carbamateYield 24%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A mixture of 3-benzyl-3-azabicyclo[3.1.0]hexane-6-carboxylic acid hydrochloride (101 mg, 0.40 mmol), triethylamine (185 mg, 1.83 mmol), DPPA (180 mg, 0.65 mmol), t-butanol (4 ml) and toluene (3 ml) was heated under reflux in a nitrogen atmosphere for 23 hours, followed by cooling the reaction mixture, pouring it into water, extracting with toluene, washing the organic layer successively with an aqueous solution of sodium carbonate, water and a saturated aqueous NaCl solution, drying over anhydrous magnesium sulfate, distilling off the solvent under reduced pressure, and purifying the residue according to thin-layer chromatography (developing solvent: chloroform:methanol=20:1), to obtain 3-benzyl-6-t-butoxycarbonylamino-3-azabicyclo[3.1.0]hexane (27 mg, 0.09 mmol, 24%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux in a nitrogen atmosphere for 23 hours
  3. temperatureby cooling the reaction mixture
  4. extractionextracting with toluene
  5. washwashing the organic layer successively with an aqueous solution of sodium carbonate, water
  6. dry with materiala saturated aqueous NaCl solution, drying over anhydrous magnesium sulfate
  7. distillationdistilling off the solvent under reduced pressure
  8. custompurifying the residue

Sources & evidence

ORD record
ord-dc5e1e9ef5734909a12873812a99739a
Source dataset
uspto-grants-1997_04
Patent number
US05623078

Reaction notes

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