Trimethylsilyldiazomethane → Methyl 4-(1-(tert-butoxycarbonyl)-4-(methoxycarbonyl)piperidin-4-yl)butanoate

HRID 8747

Reaction equation

HRID 8747 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])([C:14]([O:16][CH3:17])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:24][Si](C=[N+]=[N-])(C)C>ClCCl.CO>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]([CH2:18][CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])([C:14]([O:16][CH3:17])=[O:15])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 219839874-(1-(tert-Butoxycarbonyl)-4-(methoxycarbonyl)piperidin-4-yl)butanoic acid

Product 1

HCID 69183850Methyl 4-(1-(tert-butoxycarbonyl)-4-(methoxycarbonyl)piperidin-4-yl)butanoateYield 82.4%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

To a solution of 4-(1-(tert-butoxycarbonyl)-4-(methoxy-carbonyl)piperidin-4-yl)butanoic acid (23.4 g, 0.071 mol) from Step D in 3:1 dichloromethane/methanol (480 mL) at 0° C. was added a solution of trimethylsilyldiazomethane (53 mL, 0.11 mol, 2.0M in hexane). The reaction mixture was stirred for 15 min and then concentrated to afford 25.5 g. The residue was purified by flash chromatography eluting with 20–30% ethyl acetate in hexanes to give the title compound (20.1 g).

Workup

  1. concentrationconcentrated
  2. customto afford 25.5 g
  3. customThe residue was purified by flash chromatography
  4. washeluting with 20–30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-6b2aefe82fc74fb8a87e403b637a98cc
Source dataset
uspto-grants-2006_08
Patent number
US07091211B2

Linked notes

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