Benzyl Alcohol → HCID 20616878, compound

HRID 2119443Notes

Reaction equation

HRID 2119443 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH:11]([CH2:15]C(O)=O)[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC[N:21]([CH2:24]C)CC.C1C=CC(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:33])=CC=1.[CH2:43]([OH:50])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1>C1(C)C=CC=CC=1.CCOC(C)=O>[C:44]1([CH2:43][O:50][C:24]([NH:21][CH2:15][C@@H:11]2[CH2:12][CH2:13][CH2:14][C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:10]2)=[O:33])[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 22714070HCID 22714070, compound

Product 1

HCID 20616878HCID 20616878, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-{3-[(t-butoxy)carbonylamino]cyclohexyl}acetic acid (3.43 g, 13.35 mmol), Et3N (3.75 mL, 26.96 mmol) in toluene (86 mL) under N2 was added DPPA (5.8 mL, 26.96 mmol) and benzyl alcohol (4.28 mL, 41.38 mmol). The solution was heated to reflux overnight. The reaction was cooled to room temperature, diluted with EtOAc, washed (1.0N NaOH then brine), dried (MgSO4), filtered, and concentrated. Column chromatography (silica gel, hexanes/EtOAc gradient) gave the title compound (3.05 g, 63%). Mass Spectrum (ES+) (m/z) 263.1 [M−BOC].

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux overnight
  3. washwashed (1.0N NaOH
  4. dry with materialbrine), dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-687e0b4d134046bc84858e8d1b08ff45
Source dataset
uspto-grants-2004_02
Patent number
US06686376B2

Reaction notes

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