Benzyl Alcohol → HCID 67223002, compound

HRID 1912400Notes

Reaction equation

HRID 1912400 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([CH2:17][CH:18]=[CH2:19])(C(O)=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([N:22]([CH2:25]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:34])C=CC=CC=1.[CH2:44]([OH:51])[C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1>C1(C)C=CC=CC=1.CN(C)C1C=CN=CC=1.O.C(O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C:10]([CH2:17][CH:18]=[CH2:19])([NH:22][C:25]([O:51][CH2:44][C:45]2[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=2)=[O:34])[CH2:9]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

9

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 450742231,3-Piperidinedicarboxylic acid, 3-(2-propen-1-yl)-, 1-(1,1-dimethylethyl) ester

Product 1

HCID 67223002HCID 67223002, compound

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

To a solution of an optically-active compound of 3-allylpiperidine-1,3-dicarboxylic acid 1-tert-butyl ester (32.2 g) and triethylamine (33.2 ml) in toluene (320 ml) heated to 80° C. was added dropwise diphenylphosphoryl azide (33.4 ml) over 50 minutes. The reaction mixture was stirred at the same temperature for 2 hours and cooled to room temperature. To the mixture were added benzyl alcohol (24.6 ml) and 4-dimethylaminopyridine (2.9 g). The mixture was stirred at 100° C. for 21 hours and cooled to room temperature. Then, thereto were added ethanol (200 ml) and water (200 ml), and the mixture was extracted with n-hexane (200 ml). The separated organic layer was sequentially washed with saturated aqueous ammonium chloride solution (200 ml) and saturated aqueous sodium chloride solution (150 ml), and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/0 to 6/1) to give the titled compound (39.4 g).

Workup

  1. stirringThe mixture was stirred at 100° C. for 21 hours
  2. temperaturecooled to room temperature
  3. extractionthe mixture was extracted with n-hexane (200 ml)
  4. washThe separated organic layer was sequentially washed with saturated aqueous ammonium chloride solution (200 ml) and saturated aqueous sodium chloride solution (150 ml)
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=1/0 to 6/1)

Sources & evidence

ORD record
ord-b648f2daaaf64100b8d9b428e04862c5
Source dataset
uspto-grants-2013_12
Patent number
US08609647B2

Reaction notes

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