Tert-butyl 6-oxa-7-azabicyclo[3.2.2]non-8-ene-7-carboxylate → tert-butyl N-[(1S,4R)-4-hydroxycycloheptyl]carbamate

HRID 1631450노트

반응식

HRID 1631450 반응식
[CH:1]12[CH:16]=[CH:15][CH:5]([O:6][N:7]1[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3][CH2:2]2.[H][H]>[Ni]>[OH:6][C@@H:5]1[CH2:4][CH2:3][CH2:2][C@H:1]([NH:7][C:8](=[O:9])[O:10][C:11]([CH3:13])([CH3:12])[CH3:14])[CH2:16][CH2:15]1

참가 물질

4

반응물 2

HCID 21582700Tert-butyl 6-oxa-7-azabicyclo[3.2.2]non-8-ene-7-carboxylateHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 69723966tert-butyl N-[(1S,4R)-4-hydroxycycloheptyl]carbamate

시약·촉매·용매 1

HCID 935Nickel촉매

실험 절차

A Parr bottle was charged with Raney Nickel (ca. 1 g). The catalyst was washed with ethanol and suspended in ethanol (30 mL). The starting material, 23A (1.0 g, 4.44 mmol) was added and the reaction pressurized with hydrogen. After hours, TLC analysis suggests good conversion to desired product. The reaction was flushed with nitrogen and filtered through a pad of magnesium sulfate. The filter cake was rinsed well with ethanol. The ethanol solution was evaporated. The isolated material was dissolved in tetrahydrofuran to give a cloudy solution. The liquid was passed through a PTFE filter and then evaporated. The crude product was crystallized from ether-hexanes. The crystalline material was filtered off and rinsed with hexanes. Residual solvent was removed under vacuum to give 23B (780 mg, 3.40 mmol, 77% yield) as a colorless solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 6.76 (d, 1H, J=7.6 Hz); 4.36 (d, 1H, J=4.0 Hz); 3.51-3.73 (m, 1H); 3.37 (br. s, 1H); 1.69-1.91 (m, 2H); 1.45-1.66 (m, 5H); 1.37 (s, 9H); 1.06-1.34 (m, 3H).

후처리

  1. washThe catalyst was washed with ethanol
  2. waitAfter hours

출처 및 근거

ORD 기록
ord-0ef491cd6c064854b500da72d24b94c8
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08791257B2

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