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

HRID 2222452Notes

Reaction equation

HRID 2222452 reaction equation
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]

Participants

10

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4cbbd0f322c7441ab876cdbab0438a14
Source dataset
uspto-grants-2008_05
Patent number
US07371777B2

Reaction notes

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