Benzyl Alcohol → HCID 18770464, compound

HRID 1279429Notes

Reaction equation

HRID 1279429 reaction equation
C([N:3]([CH2:6]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:15])C=CC=CC=1.[CH2:25]([OH:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[C:33]([O:37][C:38]([N:40]1[CH2:45][CH2:44][CH:43]([CH2:46][CH:47]([CH2:51][CH:52]2[CH2:57][CH2:56][N:55]([C:58]([O:60][C:61]([CH3:64])([CH3:63])[CH3:62])=[O:59])[CH2:54][CH2:53]2)C(O)=O)[CH2:42][CH2:41]1)=[O:39])([CH3:36])([CH3:35])[CH3:34]>C1(C)C=CC=CC=1>[CH2:25]([O:32][C:6]([NH:3][CH:47]([CH2:51][CH:52]1[CH2:53][CH2:54][N:55]([C:58]([O:60][C:61]([CH3:64])([CH3:62])[CH3:63])=[O:59])[CH2:56][CH2:57]1)[CH2:46][CH:43]1[CH2:44][CH2:45][N:40]([C:38]([O:37][C:33]([CH3:36])([CH3:34])[CH3:35])=[O:39])[CH2:41][CH2:42]1)=[O:15])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 18770431HCID 18770431, compound

Product 1

HCID 18770464HCID 18770464, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Triethylamine (0.39 ml; 2.8 mmol), diphenylphosphoryl azide (0.61 ml; 2.8 mmol) and benzyl alcohol (0.39 ml; 3.8 mmol) were added to a solution in toluene (10 ml) of 2,2-bis[(1-tert-butoxycarbonyl-4-piperidinyl)methyl]acetic acid (850 mg; 1.9 mmol) synthesized by the above process, and the mixture was stirred for 12 hours in a bath controlled at 100° C. The reaction mixture was concentrated under reduced pressure, and the resultant concentrated residue was dissolved in ethyl acetate. This solution was washed successively with a saturated aqueous solution of sodium hydrogencarbonate and saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The resultant crude oil was purified by column chromatography on silica gel, thereby obtaining 639 mg (yield: 61%) of 2-benzyloxycarbonylamino-1,3-bis(1-tert-butoxycarbonyl-4-piperidinyl)propane as a colorless oil.

Workup

  1. customsynthesized by the above process
  2. customcontrolled at 100° C
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. dissolutionthe resultant concentrated residue was dissolved in ethyl acetate
  5. washThis solution was washed successively with a saturated aqueous solution of sodium hydrogencarbonate and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe resultant crude oil was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-e5366b9c8c1e41f3a395f29b72abd8d7
Source dataset
uspto-grants-2002_09
Patent number
US06448242B1

Reaction notes

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