Water → tert-butyl N-(4-hydroxycyclopent-2-en-1-yl)carbamate

HRID 351362Notes

Reaction equation

HRID 351362 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:13]2[CH2:14][CH:10]([CH:11]=[CH:12]2)[O:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(#N)C.O.[BH4-].[Na+]>[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo].C(OCC)(=O)C>[C:1]([O:5][C:6](=[O:7])[NH:8][CH:13]1[CH2:14][CH:10]([OH:9])[CH:11]=[CH:12]1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 6342AcetonitrileHCID 4311764Sodium borohydrideHCID 15332365Tert-butyl 2-oxa-3-azabicyclo[2.2.1]hept-5-ene-3-carboxylate

Product 1

HCID 22594589tert-butyl N-(4-hydroxycyclopent-2-en-1-yl)carbamateYield 65.1%

Reagents, catalysts & solvents 2

HCID 98885Molybdenum carbonyl (Mo(CO)6)CatalystHCID 8857Ethyl AcetateSolvent

Procedure

Molybdenum hexacarbonyl (1.46 g, 5.53 mmol) was added to a solution of the bicycle 2 (0.70 g, 3.55 mmol) in a 7:1 mature of acetonitrile and water (24 cm3). The suspension was stirred for 10 minutes at room temperature, then sodium borohydride (0.07 g, 1.85 mmol) was added and the suspension was heated under reflux for 3 hours. Upon completion of reaction, the mixture was allowed to cool to room temperature, filtered through a celite plug, and evaporated to dryness to give a dark oil. Flash chromatography (SiO2, 50% ethyl acetate in petrol) gave the alcohol 3 (0.46 g, 2.31 mmol, 65%) as a colourless oil; δH (200 MHz, CDCl3) 5.97 (1H, m, CH═CH), 5.85 (1H, dt, J 5.8 & 1.8 Hz, CH═CH), 4.80 (1H, m), 4.69 (1H, m), 4.42 (1H, m), 2.74 (2H, dt, J 14.3 & 7.1 Hz, CH2), 1.55 (1H, m, OH), 1.44 (9H, s, CO2C(CH3)3); m/z (CI) Found [MH]+ 200.1285 ([MH]+ C10H18NO3 requires 200.1287).

Workup

  1. temperaturethe suspension was heated
  2. temperatureunder reflux for 3 hours
  3. customUpon completion of reaction
  4. temperatureto cool to room temperature
  5. filtrationfiltered through a celite plug
  6. customevaporated to dryness
  7. customto give a dark oil

Sources & evidence

ORD record
ord-370f124f3ce74ae997e0b4099294faf7
Source dataset
uspto-grants-2007_02
Patent number
US07183440B2

Reaction notes

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