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

HRID 497482Notes

Reaction equation

HRID 497482 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-dde3fa08730e4d9b8f44062616bc421c
Source dataset
uspto-grants-2005_09
Patent number
US06949546B2

Reaction notes

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