Methyl 4-(bromomethyl)benzoate → HCID 57941324, compound

HRID 1437946Notes

Reaction equation

HRID 1437946 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][C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=1>CN(C)C=O>[CH3:25][O:24][C:22](=[O:23])[C:21]1[CH:26]=[CH:27][C:18]([CH2:17][N:3]2[C:4](=[O:15])[C:5]3[C@@H:6]4[C:11]([CH3:12])([CH3:13])[C@@:9]([CH3:14])([CH2:8][CH2:7]4)[C:10]=3[N:2]2[CH3:1])=[CH:19][CH:20]=1

Participants

4

Reactant 2

HCID 256687Methyl 4-(bromomethyl)benzoateHCID 57941341HCID 57941341, compound2×

Product 1

HCID 57941324HCID 57941324, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of (4S,7R)-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 19; 250 mg, 1.21 mmol) and methyl 4-(bromomethyl)-benzoate (0.27 g, 1.18 mmol) in N,N-dimethylformamide (12 mL) was heated at 100° C. overnight. The reaction mixture was evaporated and the residue was purified using a Biotage 40S system, eluting with 0-1% methanol/chloroform, followed by drying under high vacuum to give (4S,7R)-4-(1,7,8,8-tetramethyl-3-oxo-1,3,4,5,6,7-hexahydro-4,7-methano-indazol-2-ylmethyl)-benzoic acid methyl ester (256 mg, 61%) as a light yellow oil.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue was purified
  3. washeluting with 0-1% methanol/chloroform
  4. customby drying under high vacuum

Sources & evidence

ORD record
ord-e4fcb31af43d4f5e823c4533ce87dd8e
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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