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

HRID 54713노트

반응식

HRID 54713 반응식
C(N1[CH2:13][CH:12]2[CH:10]([CH:11]2C(O)=O)C1)C1C=CC=CC=1.[CH2:17]([N:24]1[CH2:29][CH:28]2[CH:26]([CH:27]2C(OCC)=O)[CH2:25]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[OH-:35].[Na+].C([N:39]([CH2:42]C)CC)C.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:51])=CC=1>O.C(O)(C)(C)C>[CH2:17]([N:24]1[CH2:25][CH:26]2[CH:28]([CH:27]2[NH:39][C:42]([O:51][C:12]([CH3:11])([CH3:10])[CH3:13])=[O:35])[CH2:29]1)[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 14798Sodium HydroxideHCID 199401P,P-Diphenylphosphinic azideHCID 109769003-benzyl-3-azabicyclo[3.1.0]hexane-6-carboxylic AcidHCID 15818457Ethyl 3-benzyl-3-azabicyclo[3.1.0]hexane-6-carboxylate

생성물 1

HCID 9860737tert-Butyl (3-benzyl-3-azabicyclo[3.1.0]hexan-6-yl)carbamate수율 31%

시약·촉매·용매 2

HCID 962Water용매HCID 6386tert-Butanol용매

실험 절차

A mixture of 3-benzyl-3-azabicyclo[3.1.0]hexane-6-carboxylic acid (116 mg, 0.53 mmol) obtained by treating ethyl 3-benzyl-3-azabicyclo[3.1.0]hexane-6-carboxylate obtained in step 5 of Example 1, with an aqueous solution of NaOH, with triethylamine (239 mg, 2.36 mmol), DPPA (303 mg, 1.10 mmol) and t-butanol (4 ml), was heated under reflux in a nitrogen atmosphere for 19 hours, followed by cooling the reaction mixture, pouring it into water, extracting with toluene, washing the organic layer successively with an aqueous solution of Na2CO3, water and a saturated aqueous solution of NaCl, 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 (47 mg, 0.16 mmol, 31%).

후처리

  1. customobtained
  2. temperatureunder reflux in a nitrogen atmosphere for 19 hours
  3. temperatureby cooling the reaction mixture
  4. extractionextracting with toluene
  5. washwashing the organic layer successively with an aqueous solution of Na2CO3, water
  6. dry with materiala saturated aqueous solution of NaCl, drying over anhydrous magnesium sulfate
  7. distillationdistilling off the solvent under reduced pressure
  8. custompurifying the residue

출처 및 근거

ORD 기록
ord-93f82efbd2724d1aa10420fc76ad47ba
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05623078

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