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

HRID 351362노트

반응식

HRID 351362 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 98885Molybdenum carbonyl (Mo(CO)6)촉매HCID 8857Ethyl Acetate용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-370f124f3ce74ae997e0b4099294faf7
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07183440B2

반응 노트

불러오는 중…