tert-Butanol → [(2r,3r)-2-Styryl-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl ester

HRID 1169230Notes

Reaction equation

HRID 1169230 reaction equation
[CH:1]([C@@H:9]1[C@H:14](C(O)=O)[CH2:13][CH2:12][CH2:11][O:10]1)=[CH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.C([N:20]([CH2:23]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:32])C=CC=CC=1.[C:42]([OH:46])([CH3:45])([CH3:44])[CH3:43]>>[C:42]([O:46][C:23](=[O:32])[NH:20][C@@H:14]1[CH2:13][CH2:12][CH2:11][O:10][C@@H:9]1[CH:1]=[CH:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)([CH3:45])([CH3:44])[CH3:43]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 69748371(2R,3R)-2-Styryl-tetrahydro-pyran-3-carboxylic acid

Product 1

HCID 69748163[(2r,3r)-2-Styryl-tetrahydro-pyran-3-yl]-carbamic acid tert-butyl esterYield 55.5%

Conditions

Temperature
23 °C

Procedure

To a stirring solution of (2R,3R)-2-styryl-tetrahydro-pyran-3-carboxylic acid (106 mg, 0.456 mmol) in anhydrous tert-butanol (5 mL) under nitrogen in a flame-dried round bottom flask was added sequentially triethylamine (95 μL, 0.684 mmol) and diphenylphosphoryl azide (98 μL, 0.456 mmol). The reaction was warmed to reflux conditions and maintained at reflux for 15 h . The reaction solution was then cooled to 23° C., concentrated, and purified by flash chromatography (SiO2, 30% ethyl acetate in hexanes) to yield the desired carbamate (76.4 mg, 55.5%) as a white solid. MS (ESI), m+/z: (M+H)+=304.3.

Workup

  1. temperatureThe reaction was warmed
  2. temperatureto reflux conditions
  3. temperaturemaintained
  4. temperatureat reflux for 15 h
  5. concentrationconcentrated
  6. custompurified by flash chromatography (SiO2, 30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-c03e9aaa0c244fe4938096d9b4b84cb6
Source dataset
uspto-grants-2003_09
Patent number
US06627629B2

Reaction notes

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