Potassium tert-butoxide → HCID 66638929, compound

HRID 1094462Notes

Reaction equation

[Br-].[CH2:2]([O:4][C:5]([C:7]1[C:8]([CH2:13][P+](C)(C)C)=[N:9][CH:10]=[CH:11][CH:12]=1)=[O:6])C.CC(C)([O-])C.[K+].[CH2:24]([N:31]([CH2:43][C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1)[C@H:32]([CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[F:42])[CH:33]=O)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>CCOCC>[CH3:2][O:4][C:5](=[O:6])[C:7]1[CH:12]=[CH:11][CH:10]=[N:9][C:8]=1/[CH:13]=[CH:33]/[C@H:32]([N:31]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:43][C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1)[CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[F:42]

Participants

Conditions

Temperature: -78 °C

Procedure

To a suspension of (3-ethoxycarbonyl-pyridin-2-ylmethyl)-trimethyl-phosphonium bromide (0.9 g, 2.6 mmol) in 50 mL of ether is added potassium tert-butoxide (0.32 g, 2.9 mmol) and the reaction is heated at reflux for 30 minutes. The reaction is then cooled to −78° C., a solution of (R)-2-dibenzylamino-3-(2-fluoro-phenyl)-propionaldehyde (1.8 g, 3.5 mmol) in 10 mL of ether is added, and the reaction is allowed to stir at room temperature for 16 hours. The reaction is then concentrated under reduced pressure and purification of the resultant residue by silica gel flash column chromatography gives the title compound.

Workup

temperaturethe reaction is heated
temperatureat reflux for 30 minutes
concentrationThe reaction is then concentrated under reduced pressure and purification of the resultant residue by silica gel flash column chromatography

Sources & evidence

ORD record: ord-93ca0d519ed54805b99dbc8f75466319
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08133907B2

Reaction notes

Loading…