Diisopropylamine → Methyl 2-[4-(t-butoxycarbonylaminomethyl)-benzyl]-tetrahydro-2-furancarboxylate

HRID 2222452

반응식

HRID 2222452 반응식
C(NC(C)C)(C)C.C([Li])CCC.[O:13]1[CH2:17][CH2:16][CH2:15][CH:14]1[C:18]([O:20][CH3:21])=[O:19].Br[CH2:23][C:24]1[CH:38]=[CH:37][C:27]([CH2:28][NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:26][CH:25]=1.[Cl-].[NH4+]>O1CCCC1.CCCCCC.O.C(OCC)(=O)C>[C:32]([O:31][C:30]([NH:29][CH2:28][C:27]1[CH:37]=[CH:38][C:24]([CH2:23][C:14]2([C:18]([O:20][CH3:21])=[O:19])[CH2:15][CH2:16][CH2:17][O:13]2)=[CH:25][CH:26]=1)=[O:36])([CH3:35])([CH3:33])[CH3:34]

참가 물질

10

반응물 5

HCID 7912DiisopropylamineHCID 25517Ammonium ChlorideHCID 169922Methyl tetrahydrofuran-2-carboxylateHCID 23447255tert-Butyl 4-(bromomethyl)benzylcarbamateHCID 178418339Butyllithium

생성물 1

HCID 59712499Methyl 2-[4-(t-butoxycarbonylaminomethyl)-benzyl]-tetrahydro-2-furancarboxylate수율 68.8%

시약·촉매·용매 4

HCID 962Water용매HCID 8028Tetrahydrofuran용매3회HCID 8058Hexane용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of diisopropylamine in 10 ml of tetrahydrofuran was added 5.5 ml of 1.6 M solution of n-butyllithium in hexane at −78° C. under an atmosphere of nitrogen gas. After stirring for 30 minutes, a solution of 1.17 g of methyl tetrahydro-2-furancarboxylate in 10 ml of tetrahydrofuran was added dropwise. After stirring for further 30 minutes, a solution of 1.20 g of t-butyl N-[4-(bromomethyl)benzyl]carbamate in 20 ml of tetrahydrofuran was added dropwise, and the mixture was stirred at −78° C. for 3 hours. 50 ml of saturated aqueous ammonium chloride, 200 ml of ethyl acetate and 100 ml of water were added, and the organic layer was dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography, to give 0.961 g of the title compound.

후처리

  1. stirringAfter stirring for further 30 minutes
  2. stirringthe mixture was stirred at −78° C. for 3 hours
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-4cbbd0f322c7441ab876cdbab0438a14
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07371777B2

연결된 노트

불러오는 중…