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Carbon Dioxide → [Rac]-(4-tert-butyl-benzyl)-[2-(4-chloro-phenyl)-2-fluoro-ethyl]-amine

HRID 855208
Notes
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Reaction equation

HRID 855208 reaction equation
[C:1]([C:5]1[CH:22]=[CH:21][C:8]([CH2:9][NH:10][CH2:11][CH:12]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CCN(S(F)(F)[F:29])CC.C(=O)(O)[O-].[Na+].C(=O)=O>C(Cl)Cl>[C:1]([C:5]1[CH:22]=[CH:21][C:8]([CH2:9][NH:10][CH2:11][CH:12]([C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=2)[F:29])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium BicarbonateHCID 69342320[Rac]-(4-tert-butyl-benzyl)-[2-(4-chloro-phenyl)-2-hydroxy-ethyl]-amine

Product 1

HCID 69341923[Rac]-(4-tert-butyl-benzyl)-[2-(4-chloro-phenyl)-2-fluoro-ethyl]-amine

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Conditions

Temperature
0 °C

Procedure

159 mg of [rac]-(4-tert-butyl-benzyl)-[2-(4-chloro-phenyl)-2-hydroxy-ethyl]-amine (0.5 mmol, described in example S43) in 5 ml DCM was cooled to 2° C. and treated with 0.2 ml of DAST (1.5 mmol) for 2 min. After 2 h stirring at 0° C. followed by 1 h at rt, the reaction mixture was again cooled down to 0° C. and treated with 5 ml saturated aqueous sodium bicarbonate. The reaction mixture was stirred until CO2 evolution stopped, then the organic phase was separated, washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue was Purified by silicagel chromatography (40 g silica gel; heptane/EtOAc 2:1) leading to 27 mg of a light yellow semi-solid (17%). M(ISP) 320.3 (M+H)+.

Workup

  1. customwas cooled to 2° C.
  2. waitfollowed by 1 h at rt
  3. temperaturethe reaction mixture was again cooled down to 0° C.
  4. customthe organic phase was separated
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was Purified by silicagel chromatography (40 g silica gel; heptane/EtOAc 2:1)

Sources & evidence

ORD record
ord-27a180282cf84049863479db9e48078d
Source dataset
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07259183B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes