Methyl 2-(bromomethyl)benzoate → HCID 57941519, compound

HRID 1438087Notes

Reaction equation

HRID 1438087 reaction equation
[CH3:1][N:2]1[C:10]2[C@@:9]3([CH3:14])[C:11]([CH3:13])([CH3:12])[C@H:6]([CH2:7][CH2:8]3)[C:5]=2[C:4](=[O:15])[NH:3]1.Br[CH2:17][C:18]1[CH:27]=[CH:26][CH:25]=[CH:24][C:19]=1[C:20]([O:22][CH3:23])=[O:21]>CN(C)C=O>[CH3:23][O:22][C:20](=[O:21])[C:19]1[CH:24]=[CH:25][CH:26]=[CH:27][C:18]=1[CH2:17][N:3]1[C:4](=[O:15])[C:5]2[C@@H:6]3[C:11]([CH3:12])([CH3:13])[C@@:9]([CH3:14])([CH2:8][CH2:7]3)[C:10]=2[N:2]1[CH3:1]

Participants

4

Reactant 2

HCID 2734813Methyl 2-(bromomethyl)benzoateHCID 57941341HCID 57941341, compound2×

Product 1

HCID 57941519HCID 57941519, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (4S,7R)-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 19; 300 mg, 1.5 mmol) and methyl 2-bromomethyl-benzoate (370 mg, 1.6 mmol) in dimethylformamide (15 mL) was heated at ˜100° C. for 2 days. The reaction mixture was allowed to cool and the solvent was evaporated. The residue was taken up in dichloromethane and purified on a Biotage 40S system, eluting with 0-2% methanol/dichloromethane to give 2-((4S,7R)-1,7,8,8-tetramethyl-3-oxo-1,3,4,5,6,7-hexahydro-4,7-methano-indazol-2-ylmethyl)-benzoic acid methyl ester (304 mg, 59%) as an orange oil. 1H NMR indicated that it contained minor impurities. It was used in the next step without further purification.

Workup

  1. temperatureto cool
  2. customthe solvent was evaporated
  3. custompurified on a Biotage 40S system
  4. washeluting with 0-2% methanol/dichloromethane

Sources & evidence

ORD record
ord-73720a793ac0470fbe20906aa31a4998
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

Loading…