Ammonium Chloride → HCID 178477574, compound

HRID 853133Notes

Reaction equation

HRID 853133 reaction equation
[CH2:1]([NH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]([O:24][Si:25]([CH2:30][CH3:31])([CH2:28][CH3:29])[CH2:26][CH3:27])([C:20]([F:23])([F:22])[F:21])[C:16]([F:19])([F:18])[F:17])[CH2:11][CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[CH:41]1([C:44](Cl)=O)[CH2:43][CH2:42]1.[NH4+].[Cl-]>C(Cl)Cl.C1COCC1.CCOCC>[CH2:1]([N:8]([CH2:44][CH:41]1[CH2:43][CH2:42]1)[C@H:9]1[CH2:14][CH2:13][C@H:12]([C:15]([O:24][Si:25]([CH2:28][CH3:29])([CH2:30][CH3:31])[CH2:26][CH3:27])([C:20]([F:21])([F:22])[F:23])[C:16]([F:18])([F:19])[F:17])[CH2:11][CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 77637Cyclopropanecarbonyl chlorideHCID 81531DiisopropylethylamineHCID 178477573HCID 178477573, compound

Product 1

HCID 178477574HCID 178477574, compoundYield 110.4%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 930 mg (1.73 mmol) of trans benzyl-[4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-cyclohexyl]-amine (example 3.1) in 2 mL of CH2Cl2 was treated with 0.6 mL (3.5 mmol) of DIPEA and 0.23 mL (2.56 mmol) of cyclopropylcarbonylchloride. The mixture was stirred at RT overnight and distributed between a saturated aqueous solution of NH4Cl and Et2O. The combined organic phases were dried over Na2SO4, and the solvent was evaporated. The crude material obtained was dissolved in 10 mL of THF, treated with 3.46 mL of a 1M BH3-solution in THF and refluxed for 6 hrs. Distribution between a diluted aqueous solution of NaOH and Et2O, drying of the combined organic phases over Na2SO4 and evaporation of the solvent gave 1 g of crude trans benzyl-cyclopropylmethyl-[4-(2,2,2-trifluoro-1-triethylsilanyloxy-1-trifluoromethyl-ethyl)-cyclohexyl]-amine as a yellow oil, MS: 524 (M+H)+.

Workup

  1. dry with materialThe combined organic phases were dried over Na2SO4
  2. customthe solvent was evaporated
  3. customThe crude material obtained
  4. temperaturerefluxed for 6 hrs
  5. dry with materialDistribution between a diluted aqueous solution of NaOH and Et2O, drying of the combined organic phases over Na2SO4 and evaporation of the solvent

Sources & evidence

ORD record
ord-bc02f105596b495b8b159f12935ce4ed
Source dataset
uspto-grants-2007_08
Patent number
US07253282B2

Reaction notes

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