Benzyl Alcohol → HCID 68851088, compound

HRID 1984051Notes

Reaction equation

HRID 1984051 reaction equation
Br[C:2]1[CH:20]=[CH:19][C:5]([C:6]([NH:8][CH:9]2[C:14]([CH3:16])([CH3:15])[C@H:13]3[CH2:17][C@:10]2([CH3:18])[CH2:11][CH2:12]3)=[O:7])=[CH:4][C:3]=1[S:21]([N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)(=[O:23])=[O:22].[CH2:30]([OH:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.C(OCC)(=O)C>CN(C)C=O>[CH2:30]([O:37][C:2]1[CH:20]=[CH:19][C:5]([C:6]([NH:8][CH:9]2[C:14]([CH3:16])([CH3:15])[C@H:13]3[CH2:17][C@:10]2([CH3:18])[CH2:11][CH2:12]3)=[O:7])=[CH:4][C:3]=1[S:21]([N:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1)(=[O:23])=[O:22])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 244Benzyl AlcoholHCID 8857Ethyl AcetateHCID 68852883HCID 68852883, compound

Product 1

HCID 68851088HCID 68851088, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

4-Bromo-3-(morpholinosulfonyl)-N-((1S,4R)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl)benzamide (2.4.AaBa, 1.00 g, 2.06 mmol) benzyl alcohol (3.1, 0.256 mL, 0.00247 mol) were dissolved in 10 mL dimethylformamide. The reaction was heated to 100° C. for 18 hours. Ethyl acetate (20 mL) was added and aqueous workup was performed. The organic layer was dried over magnesium sulfate evaporated and purified via SiO2 chromatography (16%-33% ethyl acetate/hexane) to yield 4-(benzyloxy)-3-(morpholinosulfonyl)-N-((1S,4R)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl)benzamide (2I) as a white solid. MS analysis (m+1)=513.7.

Workup

  1. dry with materialThe organic layer was dried over magnesium sulfate
  2. customevaporated
  3. custompurified via SiO2 chromatography (16%-33% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-5815412d583b4e649b2c001ce22cc494
Source dataset
uspto-grants-2009_06
Patent number
US07544676B2

Reaction notes

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