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

HRID 1846754ノート

反応式

HRID 1846754 の反応式
[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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-654092b370954f62b6ac3cd8c5ffb2a7
出典データセット
uspto-grants-2015_02
特許番号
US08952037B2

反応ノート

読み込み中…