Ammonium Chloride → HCID 67458995, compound

HRID 625067Notes

Reaction equation

HRID 625067 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.[F-].[Si]([O:26][CH2:27][CH:28]([C:37]1([NH:40][C:41](=[O:47])[O:42][C:43]([CH3:46])([CH3:45])[CH3:44])[CH2:39][CH2:38]1)[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=1)(C(C)(C)C)(C)C.[NH4+].[Cl-]>C1COCC1>[Cl:36][C:33]1[CH:34]=[CH:35][C:30]([CH2:29][CH:28]([C:37]2([NH:40][C:41](=[O:47])[O:42][C:43]([CH3:45])([CH3:44])[CH3:46])[CH2:39][CH2:38]2)[CH2:27][OH:26])=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 67459820HCID 67459820, compound

Product 1

HCID 67458995HCID 67458995, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

TBAF (2.80 g, 8.86 mmol) was added to a stirred solution of tert-butyl 1-(1-(tert-butyldimethylsilyloxy)-3-(4-chlorophenyl)propan-2-yl)cyclopropylcarbamate (1.95 g, 4.43 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)-3-hydroxypropan-2-yl)cyclopropylcarbamate (1.25 g, 87%) as a white solid. LCMS: 325.9 [M+H+] (APCI+); Rf: 3.75 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-e5fbfd8f0f374bd68f67e0e6ee29f9ad
Source dataset
uspto-grants-2016_04
Patent number
US09303040B2

Reaction notes

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