Benzyl chloroformate → HCID 58828629, compound

HRID 1711404Notes

Reaction equation

HRID 1711404 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[C:17]([CH2:24][S:25]([C:28]3[C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH:31]=[CH:30][CH:29]=3)(=[O:27])=[O:26])[CH:16]=2)[CH2:10][CH2:9]1)C1C=CC=CC=1.[CH2:38]([O:45][C:46](Cl)=[O:47])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.[OH-].[Na+]>C1C=CC=CC=1>[CH2:38]([O:45][C:46]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[C:17]([CH2:24][S:25]([C:28]3[C:37]4[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=4)[CH:31]=[CH:30][CH:29]=3)(=[O:26])=[O:27])[CH:16]=2)[CH2:10][CH2:9]1)=[O:47])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 14798Sodium HydroxideHCID 58828636HCID 58828636, compound

Product 1

HCID 58828629HCID 58828629, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 1-benzyl-4-[3-(1-naphthylsulfonylmethyl)-4-nitrophenoxy]-piperidine (4.7 g, 9.1 mmol) and benzylchloroformate (6.0 mL, 42 mmol) in benzene was heated at reflux temperature, under nitrogen, for 3 hours, cooled to ambient temperatures, poured into 2.5 N sodium hydroxide and extracted with ethyl acetate. The extracts were combined, washed with water and brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The resultant residue was purified by flash chromatography using 30-50% ethyl acetate in hexane to afford 4-[3-(naphthalene-1-sulfonylmethyl)-4-nitro-phenoxy]-piperidine-1-carboxylic acid benzyl ester as a buff foam/amber gum, 3.9 g, 76%); Mass spectrum (+EI, [M+H]+) m/z 561. 1HNMR (500 MHz, DMSO-d6): δ8.44-8.46 (m, 1H), 8.30 (d, 1H, J=8.17 Hz), 8.07-8.10 (m, 1H), 7.94-7.99 (m, 2H), 7.61-7.68 (m, 3H), 7.27-7.37 (m, 5H), 7.09 (dd, 1H, J=9.15 Hz and 2.81 Hz), 6.72 (d, 1H, J=2.81 Hz), 5.23 (s, 2H), 5.05 (s, 2H), 4.36-4.40 (m, 1H), 3.58-3.61 (m, 2H), 3.10-3.20 (m, 2H), 1.70-1.74 (m, 2H), 1.34-1.42 ppm (m, 2H).

Workup

  1. temperatureat reflux temperature
  2. temperaturecooled to ambient temperatures
  3. extractionextracted with ethyl acetate
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe resultant residue was purified by flash chromatography

Sources & evidence

ORD record
ord-e6c81cc136f9424e888fa5718d72aeb2
Source dataset
uspto-grants-2010_09
Patent number
US07790751B2

Reaction notes

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