Diazomethane → HCID 21912816, compound

HRID 1245598Notes

Reaction equation

HRID 1245598 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[NH:18][NH:17][C:16](=[O:19])[C:15]=2[CH3:20])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N+](=[CH2:23])=[N-]>CCOCC>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[NH:18][N:17]=[C:16]([O:19][CH3:23])[C:15]=2[CH3:20])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 21912822HCID 21912822, compound

Product 1

HCID 21912816HCID 21912816, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A suspension of 1-tert-butoxycarbonyl-4-(4-methyl-(1H)-pyrazol-3-one-5-yl)piperidine (from Step C) in 12.5 mL (9.9 mmol) of 0.8 M diazomethane in Et2O was allowed to stand (occasional swirling) until all solids were in solution. Excess diazomethane was quenched with HOAc. The reaction was partitioned between 1 N NaHCO3 and Et2O. After separating phases, the organic layer was dried over MgSO4 and concentrated. The residue was purified by flash chromatography using 19:1 v/v hexanes/acetone, 9:1 v/v hexanes/acetone and 4:1 v/v hexanes/acetone as the gradient to afford the title compound as a yellow oil: RF: 0.18 (4:1 v/v hexanes/acetone); 1H-NMR (500 MHz) δ 1.48 (s, 9H), 1.57–1.65 (m, 2H), 1.82–1.85 (m, 2H), 1.89 (s, 3H), 2.70–2.79 (m, 3H), 3.91 (s, 3H), 4.24 (m, 2H)-; 13C-NMR (125 MHz) δ 55.7 (O—CH3).

Workup

  1. customExcess diazomethane was quenched with HOAc
  2. customThe reaction was partitioned between 1 N NaHCO3 and Et2O
  3. customAfter separating phases
  4. dry with materialthe organic layer was dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-4011dafc89cb43ce90e75a03dd7b0f50
Source dataset
uspto-grants-2006_10
Patent number
US07125887B2

Reaction notes

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