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

HRID 2222452ノート

反応式

HRID 2222452 の反応式
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]

参加物

10

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒3 回HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-4cbbd0f322c7441ab876cdbab0438a14
出典データセット
uspto-grants-2008_05
特許番号
US07371777B2

反応ノート

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