Trimethylsilyldiazomethane → HCID 18723536, compound

HRID 842219Notes

Reaction equation

HRID 842219 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. 1H NMR (CDCl3) δ (key peaks) 7.87-7.91 (m, 3H), 7.47-7.56 (m, 4H), 7.15-7.18 and 7.08-7.11 (m, 2H), 6.98 and 6.95 (t, 2H, J=8.5 Hz),3.79 and 3.62 (s, 3H1); Mass Spectrum (ESI) m/e=475 (M+1).

Workup

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

Sources & evidence

ORD record
ord-20954c5b18cf4978a400bbdceb1a1933
Source dataset
uspto-grants-2002_04
Patent number
US06372764B1

Reaction notes

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