Sodium Bicarbonate → HCID 178451170, compound

HRID 1755033Notes

Reaction equation

HRID 1755033 reaction equation
COCCN(S(F)(F)[F:11])CCOC.[C:14]([O:18][C:19]([C@H:21]1[CH2:26][CH2:25][C@@H:24]([O:27][CH2:28][CH2:29][CH2:30]O)[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15].C(=O)(O)[O-].[Na+]>ClCCl>[C:14]([O:18][C:19]([C@H:21]1[CH2:26][CH2:25][C@@H:24]([O:27][CH2:28][CH2:29][CH2:30][F:11])[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 2734690(Bis(2-methoxyethyl)amino)sulfur trifluorideHCID 178451171HCID 178451171, compound

Product 1

HCID 178451170HCID 178451170, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Deoxo-Fluor (5 mg, 0.02 mmol) was added to a solution of cis-4-(3-hydroxy-propoxy)-cyclohexanecarboxylic acid tert-butyl ester (3.9 mg, 0.015 mmol) in dichloromethane (0.1 ml), and the mixture was stirred at room temperature for two hours. An aqueous sodium bicarbonate solution was added to the reaction mixture, followed by extraction with dichloromethane. The organic layer was then dried over MgSO4 and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give cis-4-(3-fluoro-propoxy)-cyclohexanecarboxylic acid tert-butyl ester (3.1 mg, 79%).

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. dry with materialThe organic layer was then dried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-c18f8eaad58e4ada95186ae9f948617f
Source dataset
uspto-grants-2015_10
Patent number
US09169254B2

Reaction notes

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