Diisopropylethylamine → tert-Butyl [3-(benzyloxy)cyclobutyl]carbamate

HRID 1846754노트

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HRID 1846754 반응식
[CH2:1]([O:8][CH:9]1[CH2:12][CH:11](C(O)=O)[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:23])=CC=1.C([N:36]([CH:39](C)C)CC)(C)C.[CH3:42][C:43]([CH3:46])([O-:45])[CH3:44].[K+]>C1(C)C=CC=CC=1.C1COCC1.O.CCOC(C)=O>[CH2:1]([O:8][CH:9]1[CH2:10][CH:11]([NH:36][C:39](=[O:23])[O:45][C:43]([CH3:46])([CH3:44])[CH3:42])[CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

9

반응물 4

HCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 128151113-(Benzyloxy)cyclobutane-1-carboxylic acidHCID 23665647Potassium tert-butoxide

생성물 1

HCID 53415284tert-Butyl [3-(benzyloxy)cyclobutyl]carbamate수율 75%

시약·촉매·용매 4

HCID 962Water용매HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A solution of 3-(benzyloxy)cyclobutanecarboxylic acid (3.40 g, 16.49 mmol), DPPA (4.62 mL, 21.43 mmol), and diisopropylethylamine (3.73 mL, 21.43 mmol) in toluene (35 mL) under argon was warmed to 80° C. and stirred for 7 h, then cooled to RT. The mixture was cooled to 0° C. and then added slowly via canula to a suspension of potassium tert butoxide (3.70 g, 33.0 mmol) in THF (50 mL) under argon held at RT. The mixture was then stirred for 1 h and EtOAc and water were then added. The layers were separated, and the organic layer was dried (MgSO4), filtered, and concentrated to give an oil. The oil was purified by silica gel chromatography (0 to 50% EtOAc/hexane gradient) to give product as a white solid (3.42 g, 75%).

후처리

  1. temperatureThe mixture was cooled to 0° C.
  2. customheld at RT
  3. stirringThe mixture was then stirred for 1 h
  4. customThe layers were separated
  5. dry with materialthe organic layer was dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give an oil
  9. customThe oil was purified by silica gel chromatography (0 to 50% EtOAc/hexane gradient)

출처 및 근거

ORD 기록
ord-654092b370954f62b6ac3cd8c5ffb2a7
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08952037B2

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