Methanol → HCID 58777996, compound

HRID 1371527Notes

Reaction equation

HRID 1371527 reaction equation
[O-]S(C(F)(F)F)(=O)=O.[CH2:9]([O:11][C:12]([CH:14]1[CH2:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]([CH3:25])([CH3:24])[NH:15]1)=[O:13])[CH3:10].C[Si](C=[N+]=[N-])(C)C.[CH3:33][OH:34]>C(Cl)Cl>[CH2:9]([O:11][C:12]([CH:14]1[CH2:23][C:22]2[C:17](=[CH:18][CH:19]=[C:20]([O:34][CH3:33])[CH:21]=2)[C:16]([CH3:24])([CH3:25])[NH:15]1)=[O:13])[CH3:10]

Participants

6

Reactant 4

HCID 887MethanolHCID 167693TrimethylsilyldiazomethaneHCID 2758875TrifluoromethanesulfonateHCID 58777921HCID 58777921, compound

Product 1

HCID 58777996HCID 58777996, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the triflate salt of 1,1-dimethyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid ethyl ester (1.5 g, 3.76 mmol, 1.0 eq.) in MeOH (20 mL) and CH2Cl2 (2 mL) at 0° C. was added a solution of (trimethylsilyl)diazomethane (2.0 M in hexane, 3.7 mL, 2.0 eq.). The resulting mixture was warmed to r.t. and stirred overnight, and then the solution was concentrated. Purification by flash chromatography (125 g SiO2 linear gradient, 40 mL/min, 1:1 EtOAc/hexane for 33 minutes) afforded about 900 mg of the final compound (96%). LRMS (electrospray): 250.2 (M+1).

Workup

  1. concentrationthe solution was concentrated
  2. customPurification by flash chromatography (125 g SiO2 linear gradient, 40 mL/min, 1:1 EtOAc/hexane for 33 minutes)

Sources & evidence

ORD record
ord-9fd132bdab914af9b5951bd7bb7ecca3
Source dataset
uspto-grants-2007_01
Patent number
US07157463B2

Reaction notes

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