Hydrochloric Acid → HCID 57890137, compound

HRID 1819947Notes

Reaction equation

HRID 1819947 reaction equation
B1(C)OC(C2C=CC=CC=2)(C2C=CC=CC=2)[C@@H]2N1CCC2.[CH2:22]([C:24]([C:33]1[CH:46]=[CH:45][C:36]([O:37][CH2:38][C:39](=[O:44])[C:40]([CH3:43])([CH3:42])[CH3:41])=[C:35]([CH3:47])[CH:34]=1)([C:27]1[S:28][CH:29]=[C:30]([CH3:32])[CH:31]=1)[CH2:25][CH3:26])[CH3:23].CO.Cl>C1COCC1>[CH2:22]([C:24]([C:33]1[CH:46]=[CH:45][C:36]([O:37][CH2:38][CH:39]([OH:44])[C:40]([CH3:41])([CH3:43])[CH3:42])=[C:35]([CH3:47])[CH:34]=1)([C:27]1[S:28][CH:29]=[C:30]([CH3:32])[CH:31]=1)[CH2:25][CH3:26])[CH3:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 9838490(R)-2-Methyl-CBS-oxazaborolidineHCID 57890096HCID 57890096, compound

Product 1

HCID 57890137HCID 57890137, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of (R)-2-methyl-CBS-oxazaborolidine (0.1 ml, 0.1 mmol, 1M in toluene), borane-N,N-dimethyl aniline complex (0.18 ml, 1 mmol) in THF (5 ml) is added a solution of 1-{4-[1-ethyl-1-(4-methyl-thiophen-2-yl)-propyl]-2-methyl-phenoxy}-3,3-dimethyl-butan-2-one (372 mg, 1 mmol) in THF (5 ml) over a period of m. The reaction is stirred at RT for 2 h and MeOH (2 ml) is added followed by 1N hydrochloric acid. The mixture is extracted with EtOAc and the organic phase is concentrated and chromatographed (Hex to 25% EtOAc/Hex) to give the title compound (305 mg, 82%).

Workup

  1. extractionThe mixture is extracted with EtOAc
  2. concentrationthe organic phase is concentrated
  3. customchromatographed (Hex to 25% EtOAc/Hex)

Sources & evidence

ORD record
ord-d08e65afe2a54b3b8e3065eef1bd1d92
Source dataset
uspto-grants-2009_10
Patent number
US07601850B2

Reaction notes

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