Ammonium Chloride → Tert-butyl 1-(1-(4-chlorophenyl)-2-hydroxyethyl)cyclopropylcarbamate

HRID 625074Notes

Reaction equation

HRID 625074 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Si]([O:26][CH2:27][CH:28]([C:36]1([NH:39][C:40](=[O:46])[O:41][C:42]([CH3:45])([CH3:44])[CH3:43])[CH2:38][CH2:37]1)[C:29]1[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=1)(C(C)(C)C)(C)C.[NH4+].[Cl-]>C1COCC1>[Cl:35][C:32]1[CH:33]=[CH:34][C:29]([CH:28]([C:36]2([NH:39][C:40](=[O:46])[O:41][C:42]([CH3:44])([CH3:43])[CH3:45])[CH2:37][CH2:38]2)[CH2:27][OH:26])=[CH:30][CH:31]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 67457795HCID 67457795, compound

Product 1

HCID 67459806Tert-butyl 1-(1-(4-chlorophenyl)-2-hydroxyethyl)cyclopropylcarbamateYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (2.8 g, 8.9 mmol) was added to a stirred solution of tert-butyl 1-(2-(tert-butyldimethylsilyloxy)-1-(4-chlorophenyl)ethyl)cyclopropylcarbamate (1.9 g, 4.5 mmol) in THF (80 mL). The mixture was stirred at room temperature for 2 hours. Saturated NH4Cl solution was added to the reaction. The mixture was extracted with ether. The combined organic layer was washed with brine, dried and concentrated. The residue was purified by column (hexane:EtOAc, 20:1 to 4:1) to give tert-butyl 1-(1-(4-chlorophenyl)-2-hydroxyethyl)cyclopropylcarbamate (1.1 g, 79%) as a white solid. LCMS: 311.8 [M+H+] (APCI+); Rf: 3.47 min.

Workup

  1. extractionThe mixture was extracted with ether
  2. washThe combined organic layer was washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column (hexane:EtOAc, 20:1 to 4:1)

Sources & evidence

ORD record
ord-4404bdef1db344bc99d62f181a95ff65
Source dataset
uspto-grants-2016_04
Patent number
US09303040B2

Reaction notes

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