Diethyl Ether → HCID 59281702, 화합물

HRID 1408939

반응식

HRID 1408939 반응식
[CH3:1]COCC.C[Li].[O:8]=[C:9]1[CH2:13][CH2:12][CH2:11][CH:10]1[NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18].[Cl-].[Ce+3].[Cl-].[Cl-]>O1CCCC1>[OH:8][C:9]1([CH3:1])[CH2:13][CH2:12][CH2:11][CH:10]1[NH:14][C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:20])[CH3:19]

참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 24636Cerium(III) chlorideHCID 357962tert-butyl N-(2-oxocyclopentyl)carbamateHCID 178418348HCID 178418348, 화합물

생성물 1

HCID 59281702HCID 59281702, 화합물수율 82%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A 1.6 M ether solution of methyllithium (13.59 mL, 21.75 mmol) was added to a stirred suspension of tert-butyl 2-oxocyclopentylcarbamate (1.97 g, 9.89 mmol, from Step 2) and cerium(III) chloride (5.36 g, 21.75 mmol) in tetrahydrofuran (50 mL) at −78° C. under nitrogen. After 2.5 h at −78° C., the mixture was quenched with saturated ammonium chloride, allowed to warm to room temperature, and filtered through a short bed of Celite to remove insoluble cerium salt. The filter cake was rinsed with ethyl acetate. The filtrated was extracted with ethyl acetate three times. The combined ethyl acetate phase was washed with saturated ammonium chloride and brine respectively, dried (MgSO4), filtered and concentrated. Silica gel chromatography, eluting with 0 to 50% ethyl acetate in hexanes, gave tert-butyl 2-hydroxy-2-methylcyclopentylcarbamate as yellow solid (1.47 g, 82% yield). 1H NMR analysis indicated the presence of approximately a 3:1 diastereomeric mixture.

후처리

  1. customthe mixture was quenched with saturated ammonium chloride
  2. filtrationfiltered through a short bed of Celite
  3. customto remove insoluble cerium salt
  4. washThe filter cake was rinsed with ethyl acetate
  5. extractionThe filtrated was extracted with ethyl acetate three times
  6. washThe combined ethyl acetate phase was washed with saturated ammonium chloride and brine respectively
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. washSilica gel chromatography, eluting with 0 to 50% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-8036fafc7a4e4e8e842ad322318190fa
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921368B2

연결된 노트

불러오는 중…