Tetrabutylammonium Fluoride → HCID 86615387, compound

HRID 1436742Notes

Reaction equation

HRID 1436742 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][O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:29][CH2:28][C@@H:27]1[CH:42]=[O:43])=[O:25])([CH3:22])([CH3:21])[CH3:20].[F:44][C:45]1[CH:50]=[C:49]([CH2:51][CH2:52][N+:53]([O-:55])=[O:54])[CH:48]=[C:47]([F:56])[CH:46]=1>O1CCCC1>[C:19]([O:23][C:24]([N:26]1[CH2:31][C@H:30]([O:32][CH2:33][O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH2:29][CH2:28][C@@H:27]1[CH:42]([OH:43])[CH:52]([N+:53]([O-:55])=[O:54])[CH2:51][C:49]1[CH:50]=[C:45]([F:44])[CH:46]=[C:47]([F:56])[CH:48]=1)=[O:25])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 2724141Tetrabutylammonium FluorideHCID 552507531,3-Difluoro-5-(2-nitroethyl)benzeneHCID 86615385HCID 86615385, compound

Product 1

HCID 86615387HCID 86615387, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add tetrabutylammonium fluoride (12.0 mL, 11.9 mmol, 1.0 M in tetrahydro-furan) to (2R, 5R)-5-Benzyloxymethoxy-2-formyl-piperidine-1-carboxylic acid 1-tert-butyl ester (8.0 g, 23.90 mmol) and 1,3-difluoro-5-(2-nitro-ethyl)-benzene (4.92 g, 26.30 mmol) in 150 mL tetrahydrofuran at room temperature, stir overnight and concentrate. Subject to silica gel chromatography, eluting with 100% hexane to 90:10 hexane: ethyl acetate) to provide the desired compound as a mixture of 3 isomers (8.0 g, 62% overall yield).

Workup

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

Sources & evidence

ORD record
ord-70889c3e782643f2b2c23ba538d460e6
Source dataset
uspto-grants-2009_11
Patent number
US07618978B2

Reaction notes

Loading…