Potassium Carbonate → ethyl (3S)-3-[4-[[4-(spiro[indene-1,4'-piperidine]-1'-ylmethyl)phenyl]methoxy]phenyl]hex-4-ynoate

HRID 390400Notes

Reaction equation

HRID 390400 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:15]#[C:16][CH3:17])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:25][C:26]1[CH:46]=[CH:45][C:29]([CH2:30][N:31]2[CH2:36][CH2:35][C:34]3([C:44]4[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=4)[CH:38]=[CH:37]3)[CH2:33][CH2:32]2)=[CH:28][CH:27]=1>C(#N)C>[N:31]1([CH2:30][C:29]2[CH:45]=[CH:46][C:26]([CH2:25][O:1][C:2]3[CH:3]=[CH:4][C:5]([C@@H:8]([C:15]#[C:16][CH3:17])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:6][CH:7]=3)=[CH:27][CH:28]=2)[CH2:36][CH2:35][C:34]2([C:44]3[C:39](=[CH:40][CH:41]=[CH:42][CH:43]=3)[CH:38]=[CH:37]2)[CH2:33][CH2:32]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 67087065Ethyl (3S)-3-(4-hydroxyphenyl)hex-4-ynoateHCID 670871851'-[4-(Bromomethyl)benzyl]spiro[indene-1,4'-piperidine]

Product 1

HCID 58230558ethyl (3S)-3-[4-[[4-(spiro[indene-1,4'-piperidine]-1'-ylmethyl)phenyl]methoxy]phenyl]hex-4-ynoateYield 38.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of ethyl(3S)-3-(4-hydroxyphenyl)hex-4-ynate (0.350 g, 1.5 mmol) in acetonitrile (25 mL) is added potassium carbonate (0.621 g, 4.5 mmol) and 1′-[4-(bromomethyl)benzyl]spiro[indene-1,4′-piperidine] (0.77 g, 2.1 mmol). The reaction mixture is heated for 16 hours at 90° C. The mixture is concentrated, diluted with water, and extracted with EtOAc (2×200 mL). The combined extracts are washed with water (50 mL), brine (50 mL), dried over sodium sulfate, filtered, and concentrated to dryness to give the title compound (0.3 g, 38%). ESI/MS m/z 520 (M+H)+.

Workup

  1. concentrationThe mixture is concentrated
  2. additiondiluted with water
  3. extractionextracted with EtOAc (2×200 mL)
  4. washThe combined extracts are washed with water (50 mL), brine (50 mL)
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-37c3d8d39fba4ade9333d18fbae73ae9
Source dataset
uspto-grants-2013_02
Patent number
US08383642B2

Reaction notes

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