Tetrabutylammonium Fluoride → HCID 86615383, compound

HRID 1436735Notes

Reaction equation

HRID 1436735 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[C:19]([O:23][C:24]([N:26]1[CH2:31][C@H:30]([O:32][CH2:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[CH2:29][CH2:28][C@@H:27]1[CH:40]=[O:41])=[O:25])([CH3:22])([CH3:21])[CH3:20].[F:42][C:43]1[CH:48]=[C:47]([CH2:49][CH2:50][N+:51]([O-:53])=[O:52])[CH:46]=[C:45]([F:54])[CH:44]=1>O1CCCC1>[C:19]([O:23][C:24]([N:26]1[CH2:31][C@H:30]([O:32][CH2:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)[CH2:29][CH2:28][C@@H:27]1[CH:40]([OH:41])[CH:50]([N+:51]([O-:53])=[O:52])[CH2:49][C:47]1[CH:48]=[C:43]([F:42])[CH:44]=[C:45]([F:54])[CH:46]=1)=[O:25])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 552507531,3-Difluoro-5-(2-nitroethyl)benzeneHCID 86615381HCID 86615381, compound

Product 1

HCID 86615383HCID 86615383, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add tetrabutylammonium fluoride (0.08 mL, 0.08 mmol, 1.0 M in tetrahydro-furan) to (2R, 5R)-5-Benzyloxy-2-formyl-piperidine-1-carboxylic acid tert-butyl ester (0.27 mg, 0.84 mmol) and 1,3-difluoro-5-(2-nitro-ethyl)-benzene (0.17 g, 0.93 mmol) in 5 mL tetrahydrofuran. Stir at room temperature overnight and concentrate. Subject the residue to silica gel chromatography, eluting with from 100% hexane to 90:10 hexane:ethyl acetate to provide the desired compound as a mixture of 3 isomers (0.286 g, 67%).

Workup

  1. concentrationconcentrate
  2. washeluting with from 100% hexane to 90:10 hexane

Sources & evidence

ORD record
ord-4b4da922bf8a47bbb029d75d2c96266b
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

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