(Diethylamino)sulfur trifluoride → Tert-butyl 2-fluoro-2-methylcyclopentylcarbamate

HRID 1408940노트

반응식

HRID 1408940 반응식
C(N(S(F)(F)[F:7])CC)C.O[C:11]1([CH3:24])[CH2:15][CH2:14][CH2:13][CH:12]1[NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20]>ClCCl>[F:7][C:11]1([CH3:24])[CH2:15][CH2:14][CH2:13][CH:12]1[NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20]

참가 물질

4

반응물 2

HCID 123472(Diethylamino)sulfur trifluorideHCID 59281702Tert-butyl 2-hydroxy-2-methylcyclopentylcarbamate

생성물 1

HCID 68291793Tert-butyl 2-fluoro-2-methylcyclopentylcarbamate수율 48.4%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(Diethylamino)sulphur trifluoride (2.75 mL, 20.84 mmol) was added to a solution of tert-butyl 2-hydroxy-2-methylcyclopentylcarbamate (2.243 g, 10.42 mmol, from Step 3) in dichloromethane (40 mL) at −78° C. under nitrogen. After 4 h at −78° C., the mixture was quenched with saturated sodium bicarbonate, allowed to warm to room temperature, and extracted with dichloromethane. The dichloromethane phase was concentrated and purified by silica gel chromatography, eluting with 0 to 50% ethyl acetate in hexanes, to give tert-butyl 2-fluoro-2-methylcyclopentylcarbamate as brown oil (1.095 g, 48% yield). 1H NMR analysis indicated approximately 3.5:1 mixture of two diastereomers.

후처리

  1. customthe mixture was quenched with saturated sodium bicarbonate
  2. extractionextracted with dichloromethane
  3. concentrationThe dichloromethane phase was concentrated
  4. custompurified by silica gel chromatography
  5. washeluting with 0 to 50% ethyl acetate in hexanes

출처 및 근거

ORD 기록
ord-a62e9107d1f64a96ab0ce6fd4b67a1b5
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08921368B2

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