Benzyl Alcohol → HCID 70981178, compound

HRID 2280812Notes

Reaction equation

HRID 2280812 reaction equation
[C:1]12(C(O)=O)[CH2:6][CH:4]([CH2:5]1)[CH2:3][CH2:2]2.CC[N:12]([CH:16](C)C)C(C)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:26])C=CC=CC=1.[C:36]1([CH2:42][OH:43])[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1>O1CCOCC1>[C:1]12([NH:12][C:16](=[O:26])[O:43][CH2:42][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[CH2:5][CH:4]([CH2:6]1)[CH2:3][CH2:2]2

Participants

6

Reactant 4

HCID 244Benzyl AlcoholHCID 81531DiisopropylethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 12603462bicyclo[2.1.1]hexane-4-carboxylic acid

Product 1

HCID 70981178HCID 70981178, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of bicyclo[2.1.1]hexane-1-carboxylic acid (1.0 g, 8.09 mmol) in dioxane (20 mL) was added DIEA (2.5 g, 12.4 mmol), diphenylphosphorylazide (3.1 g, 11.2 mmol) and phenylmethanol (1.5 g, 14.2 mmol). The mixture was stirred at 80° C. overnight under nitrogen atmosphere and concentrated under reduce pressure. The residue was purified by silica gel column chromatography (10% ethyl acetate in petroleum ether) to give the desired product (1.2 g, 5.2 mmol, yield: 65%). MS (ESI) m/z=231.2[M+H]+.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by silica gel column chromatography (10% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-9ff0b241e8014f2f9bbc04395314867d
Source dataset
uspto-grants-2015_09
Patent number
US09139534B2

Reaction notes

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