Water → (S)-tert-butyl 2-(t-butyldimethylsilyloxymethyl)aziridine-1-carboxylate

HRID 1254341

反応式

HRID 1254341 の反応式
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[C:34]([O:38][C:39]([NH:41][C@H:42]([CH2:45][O:46][Si:47]([C:50]([CH3:53])([CH3:52])[CH3:51])([CH3:49])[CH3:48])[CH2:43]O)=[O:40])([CH3:37])([CH3:36])[CH3:35].O>C1COCC1.CC#N.C1COCC1>[Si:47]([O:46][CH2:45][CH:42]1[CH2:43][N@@:41]1[C:39]([O:38][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:40])([C:50]([CH3:53])([CH3:52])[CH3:51])([CH3:49])[CH3:48]

参加物

7

反応物 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 11141286HCID 11141286、化合物

生成物 1

HCID 72525716(S)-tert-butyl 2-(t-butyldimethylsilyloxymethyl)aziridine-1-carboxylate収率 54.3%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 22177404Acetonitrile tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Ph3P (19.65 g, 75 mmol) was dissolved in 9:1 THF/CH3CN (600 mL) and cooled to 0° C., DIAD (14.7 mL, 75 mmol) was added dropwise over 15 min. After stirring for 30 min, a solution of (S)-2-(t-butoxycarbonylamino)-3-(t-butyldimethylsilyloxy)propan-1-ol (15.25 g, 50 mmol) in THF (100 mL) was added dropwise over 15 min, the reaction mixture was allowed to rt and stirred for 24 h. Water (100 mL) was added and volatiles were evaporated. The residue was partitioned between water (100 mL) and EtOAc (2×100 mL). The organic layers were washed with brine, dried over MgSO4 and evaporated. The residue was purified by silica chromatography to provide (S)-tert-butyl 2-(t-butyldimethylsilyloxymethyl)aziridine-1-carboxylate (7.8 g, 54%) as an oil. 1H NMR (CDCl3, 400 MHz): δ 0.07 (s, 6 H), 0.89 (s, 9 H), 1.45 (s, 9 H), 2.06 (d, J=3.6 Hz 1 H), 2.26 (d, J=6 Hz 1 H), 2.55 (m, 1 H), 3.64 (dd, J=16.4, 4.8 Hz, 1 H), 3.82 (dd, J=16.4, 4.4 Hz, 1 H).

後処理

  1. customwas allowed to rt
  2. stirringstirred for 24 h
  3. customvolatiles were evaporated
  4. customThe residue was partitioned between water (100 mL) and EtOAc (2×100 mL)
  5. washThe organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customThe residue was purified by silica chromatography

出典と根拠

ORDレコード
ord-066d8ceda0d84528aca1a4f1bc5192e0
出典データセット
uspto-grants-2013_06
特許番号
US08455521B2

関連ノート

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