1,2-Dichloroethane → HCID 58695790, compound

HRID 1178882Notes

Reaction equation

HRID 1178882 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH:11]2[CH2:12][CH2:13][CH:7]1[CH2:8][CH:9]([C:14]([OH:16])=[O:15])[CH2:10]2)=[O:5])[CH3:2].[CH:17]1(O)[CH2:22][CH2:21][CH2:20][CH:19]=[CH:18]1.C(Cl)CCl>ClCCl.CN(C1C=CN=CC=1)C>[CH:7]12[N:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH:11]([CH2:12][CH2:13]1)[CH2:10][CH:9]([C:14]([O:16][CH:22]1[CH2:21][CH2:20][CH2:19][CH:18]=[CH:17]1)=[O:15])[CH2:8]2

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 131982-Cyclohexen-1-OLHCID 22958903HCID 22958903, compound

Product 1

HCID 58695790HCID 58695790, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-(ethoxycarbonyl)-8-azabicyclo[3.2.1]octane-3-carboxylic acid (1-4) (1.88 g, 8.27 mmol) in dichloromethane (30.0 mL) was added 2-cyclohexen-1-ol (0.812 g, 8.27 mmol, Aldrich), EDC (2.38 g, 12.4 mmol), and DMAP (0.100 g). The mixture was stirred at room temperature overnight and quenched with EtOAc (200 mL). The organic solution was washed with a 5% aqueous HCl solution (100 mL), saturated aqueous solution of NaHCO3 (100 mL), and brine (100 mL), and dried over anhydrous MgSO4, and concentrated. Purification of the crude residue by flash chromatography over silica gel (10% ethyl acetate/hexanes as eluent) afforded (1-5) as colorless oil.

Workup

  1. customquenched with EtOAc (200 mL)
  2. washThe organic solution was washed with a 5% aqueous HCl solution (100 mL), saturated aqueous solution of NaHCO3 (100 mL), and brine (100 mL)
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated
  5. customPurification of the crude residue by flash chromatography over silica gel (10% ethyl acetate/hexanes as eluent)

Sources & evidence

ORD record
ord-112fd499baef4d3883460f0f2bb047c6
Source dataset
uspto-grants-2007_10
Patent number
US07276520B2

Reaction notes

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