4-Methoxybenzyl bromide → HCID 57941414, compound

HRID 1437942Notes

Reaction equation

HRID 1437942 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.[CH3:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Br)=[CH:20][CH:19]=1>CN(C)C=O>[CH3:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22][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:20][CH:19]=1

Participants

4

Reactant 2

HCID 1650214-Methoxybenzyl bromideHCID 57941341HCID 57941341, compound2×

Product 1

HCID 57941414HCID 57941414, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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; 102 mg, 0.49 mmol) and 4-methoxy-benzyl bromide (73 μL, 0.50 mmol) in N,N-dimethylformamide (5 mL) was stirred at room temperature overnight, then heated to 100° C. and left over the weekend. At this time it was found that the heating bath had failed and the reaction mixture was at room temperature. 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)-2-(4-methoxy-benzyl)-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (48 mg, 30%) as a white solid. APCI-MS (M+H) 327.

Workup

  1. temperatureheated to 100° C.
  2. waitleft over the weekend
  3. customwas at room temperature
  4. customThe reaction mixture was evaporated
  5. customthe residue was purified
  6. washeluting with 0-1% methanol/chloroform
  7. customby drying under high vacuum

Sources & evidence

ORD record
ord-c483824bf6124110b1a16be6001b710c
Source dataset
uspto-grants-2009_11
Patent number
US07622492B2

Reaction notes

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