Triacetoxyperiodinane → tert-butyl N-(2-oxocyclopentyl)carbamate

HRID 1408938

반응식

HRID 1408938 반응식
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH:23][C@@H:24]1[CH2:28][CH2:27][CH2:26][C@H:25]1[NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33]>ClCCl>[O:23]=[C:24]1[CH2:28][CH2:27][CH2:26][CH:25]1[NH:29][C:30](=[O:36])[O:31][C:32]([CH3:34])([CH3:33])[CH3:35]

참가 물질

4

반응물 2

HCID 159087TriacetoxyperiodinaneHCID 45091953(1R,2R)-trans-N-Boc-2-Aminocyclopentanol

생성물 1

HCID 357962tert-butyl N-(2-oxocyclopentyl)carbamate수율 68%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Dess-Martin periodinane (2.72 g, 6.41 mmol) was added to a stirred solution of tert-butyl 2-hydroxycyclopentylcarbamate (1.23 g, 6.11 mmol, from Step 1) in dichloromethane (30 mL) while the reaction container was placed in a room temperature water bath. After 1.5 h at room temperature, the mixture was quenched with 1 M aqueous sodium thiosulfate. After shaking the mixture vigorously, the dichloromethane phase was separated and concentrated. Silica gel chromatography, eluting with 0 to 50% ethyl acetate in hexanes, gave tert-butyl 2-oxocyclopentylcarbamate as white crystalline solid (824.6 mg, 68% yield). 1H NMR (400 MHz, chloroform-d) δ ppm 5.03 (1 H, br. s.), 3.90 (1 H, br. s.), 2.56 (1 H, br. s.), 2.38 (1 H, dd, J=19.15, 8.80 Hz), 2.08-2.22 (1 H, m), 1.96-2.08 (1 H, m), 1.73-1.89 (1 H, m), 1.52-1.69 (1 H, m), 1.42 (9 H, s).

후처리

  1. customwas placed in a room temperature
  2. customthe mixture was quenched with 1 M aqueous sodium thiosulfate
  3. customthe dichloromethane phase was separated
  4. concentrationconcentrated
  5. washSilica gel chromatography, eluting with 0 to 50% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-490b75cf0e09416bb3bbdab58e56bd99
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921368B2

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