Diisopropylethylamine → HCID 86635308, compound

HRID 1664499Notes

Reaction equation

HRID 1664499 reaction equation
Cl[C:2]([CH:4]1[CH2:16][C:15]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[N:8]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:7]=2[CH2:6][CH2:5]1)=[O:3].[C:23]1([C@H:29]([OH:31])[CH3:30])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CCN(C(C)C)C(C)C>C(Cl)Cl.CN(C1C=CN=CC=1)C.CCOC(C)=O>[CH2:21]([O:20][C:18]([CH2:17][N:8]1[C:7]2[CH2:6][CH2:5][CH:4]([C:2]([O:31][C@@H:29]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH3:30])=[O:3])[CH2:16][C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][CH:13]=2)=[O:19])[CH3:22]

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 6375161-Phenylethanol, (R)-HCID 86635309HCID 86635309, compound

Product 1

HCID 86635308HCID 86635308, compoundYield 76%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Crude ethyl (±)-(3-chlorocarbonyl-1,2,3,4-tetrahydro-carbazol-9-yl)-acetate (5 mmol) is dissolved in dry CH2Cl2 and treated with (R)-1-phenyl-ethanol (0.55 g, 5.4 mmol), DIEA (1.94 g, 15 mmol) and DMAP (61 mg, 0.5 mmol). The resulting yellow solution is stirred at rt overnight, diluted with EtOAc and successively washed with 0.1 N HCl, saturated aqueous NaHCO3, H2O and brine. The organic layer is dried over Na2SO4, filtered and evaporated. The residue is purified by column chromatography on silica gel (hexane/EtOAc 5:1) to provide the subtitle compound as yellow oil (1.36 g) in 76% yield.

Workup

  1. washsuccessively washed with 0.1 N HCl, saturated aqueous NaHCO3, H2O and brine
  2. dry with materialThe organic layer is dried over Na2SO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue is purified by column chromatography on silica gel (hexane/EtOAc 5:1)

Sources & evidence

ORD record
ord-e693cb1992594e159f1ccd95a0f1df6f
Source dataset
uspto-grants-2011_10
Patent number
US08039474B2

Reaction notes

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