Cesium carbonate → Ethyl (3S)-3-[4-[[4-(spiro[indane-1,4'-piperidine]-1'-ylmethyl)phenyl]methoxy]phenyl]hex-4-ynoate

HRID 390403Notes

Reaction equation

HRID 390403 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4]2([C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:8][CH2:7]2)[CH2:3][CH2:2]1.C([O-])([O-])=O.[Cs+].[Cs+].[CH2:21]([O:23][C:24](=[O:46])[CH2:25][CH:26]([C:30]1[CH:35]=[CH:34][C:33]([O:36][CH2:37][C:38]2[CH:43]=[CH:42][C:41]([CH2:44]Br)=[CH:40][CH:39]=2)=[CH:32][CH:31]=1)[C:27]#[C:28][CH3:29])[CH3:22]>C(#N)C>[N:1]1([CH2:44][C:41]2[CH:40]=[CH:39][C:38]([CH2:37][O:36][C:33]3[CH:34]=[CH:35][C:30]([C@@H:26]([C:27]#[C:28][CH3:29])[CH2:25][C:24]([O:23][CH2:21][CH3:22])=[O:46])=[CH:31][CH:32]=3)=[CH:43][CH:42]=2)[CH2:6][CH2:5][C:4]2([C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:8][CH2:7]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 156376162,3-Dihydrospiro(indene-1,4'-piperidine)HCID 670873073-[4-(4-Bromomethyl-benzyloxy)-phenyl]-hex-4-ynoic acid ethyl ester

Product 1

HCID 58230573Ethyl (3S)-3-[4-[[4-(spiro[indane-1,4'-piperidine]-1'-ylmethyl)phenyl]methoxy]phenyl]hex-4-ynoateYield 93.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2,3-dihydrospiro[indene-1,4′-piperidine] (0.37 g, 1.68 mmol) in acetonitrile (20.0 mL), is added Cs2CO3 (1.37 g, 4.21 mmol at room temperature, followed by the addition of 3-[4-(4-bromomethyl-benzyloxy)-phenyl]-hex-4-ynoic acid ethyl ester (0.70 g, 1.68 mmol). The reaction mixture is stirred overnight at room temperature. The reaction mixture is filtered through diatomaceous earth and the filtrate is evaporated. The crude product is purified by silica gel column chromatography (gradient 3% methanol in DCM) to give the title compound as colorless gel, (0.82 g, 93.7%). ESI/MS 522.2 (M+H)+.

Workup

  1. filtrationThe reaction mixture is filtered through diatomaceous earth
  2. customthe filtrate is evaporated
  3. customThe crude product is purified by silica gel column chromatography (gradient 3% methanol in DCM)

Sources & evidence

ORD record
ord-aaddc74571b04fd2972abedbeb097ddd
Source dataset
uspto-grants-2013_02
Patent number
US08383642B2

Reaction notes

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