Trimethylsilyldiazomethane → HCID 18723536, compound

HRID 2296825Notes

Reaction equation

HRID 2296825 reaction equation
[C:1]1([C:11]([N:13]2[CH2:17][CH:16]([C:18]([OH:20])=[O:19])[CH:15]([CH2:21][N:22]3[CH2:27][CH2:26][CH:25]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)[CH2:24][CH2:23]3)[CH2:14]2)=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Si](C=[N+]=[N-])(C)(C)[CH3:36]>CO.C1COCC1>[C:1]1([C:11]([N:13]2[CH2:17][CH:16]([C:18]([O:20][CH3:36])=[O:19])[CH:15]([CH2:21][N:22]3[CH2:27][CH2:26][CH:25]([C:28]4[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=4)[CH2:24][CH2:23]3)[CH2:14]2)=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 9804299HCID 9804299, compound

Product 1

HCID 18723536HCID 18723536, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.037 g (0.08 mmol) of 1-(1-naphthoyl)-3-(RS)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(SR)-carboxypyrrolidine in 0.6 mL of MeOH and 1.2 mL of THF at rt was added 0.2 mL (0.4 mmol) of TMSCHN2 (2M in hexanes) and the reaction mixture was stirred for 6 h. The reaction mixture was concentrated and the residue was purified by chromatography (silica, acetone: hexanes, 1:3) to give the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was purified by chromatography (silica, acetone: hexanes, 1:3)

Sources & evidence

ORD record
ord-d6a4abd300fd45d1aceeda0f8c8c7882
Source dataset
uspto-grants-2002_12
Patent number
US06489354B1

Reaction notes

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