Benzyl Alcohol → Benzyl [(4R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]methylcarbamate

HRID 1669823Notes

Reaction equation

HRID 1669823 reaction equation
[CH3:1][C:2]1([CH3:12])[O:6][C@H:5]([CH2:7]C(O)=O)[C:4](=[O:11])[O:3]1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:20])C=CC=CC=1.C([N:32]([CH2:35]C)CC)C.[CH2:37]([OH:44])[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH3:12][C:2]1([CH3:1])[O:6][C@H:5]([CH2:7][NH:32][C:35](=[O:20])[O:44][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:4](=[O:11])[O:3]1

Participants

7

Reactant 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 108449602-((4R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl)acetic acid

Product 1

HCID 57864461Benzyl [(4R)-2,2-dimethyl-5-oxo-1,3-dioxolan-4-yl]methylcarbamate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5.25 g intermediate from Step A above, 8.88 g diphenylphosphoryl azide, and 3.34 g triethyl amine in 100 mL toluene was refluxed under nitrogen for 75 minutes. Benzyl alcohol (2.92 g) was added and reflux continued for additional 15 hours. The reaction mixture was cooled, diluted with ethyl acetate, washed with 5% NaHCO3 and saturated brine, dried over anhydrous Na2SO4, and evaporated under vacuum to give a crude product. It was purified on silica gel with 20˜45% ethyl acetate in hexanes to give the title compound as a yellow oil. 1H NMR (CDCl3, 500 MHz) δ 7.33˜7.40 (m, 5H), 5.175 (d, J=12.1 Hz, 1H), 5.11 (d, J=11.9 Hz, 1H), 4.50˜4.52 (m, 1H), 3.69˜3.75 (m, 1H), 3.60˜3.66 (m, 1H), 1.59 (s, 3H), 1.57 (s, 3H).

Workup

  1. temperaturereflux
  2. temperatureThe reaction mixture was cooled
  3. washwashed with 5% NaHCO3 and saturated brine
  4. dry with materialdried over anhydrous Na2SO4
  5. customevaporated under vacuum
  6. customto give a crude product
  7. customIt was purified on silica gel with 20˜45% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-393d5d7c531a48ef9451166ac0b0bfe4
Source dataset
uspto-grants-2011_08
Patent number
US07989475B2

Reaction notes

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