Ammonium Chloride → (S)-N-Boc-2-ethynylpyrrolidine

HRID 17173노트

반응식

HRID 17173 반응식
Br[C:2](Br)=[CH:3][C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].C([Li])(CC)C.[Cl-].[NH4+]>C1COCC1.CCOCC>[C:3]([C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])#[CH:2]

참가 물질

6

반응물 3

HCID 25517Ammonium ChlorideHCID 14730281(S)-t-butyl 2-(2,2-dibromovinyl)pyrrolidine-1-carboxylateHCID 178418400CID 53628100

생성물 1

HCID 11030701(S)-N-Boc-2-ethynylpyrrolidine

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

A solution of Example 538A (6.11 g, 17.21 mmol) in THF (150 mL) at −78° C. was treated with sec-butyl lithium (24.6 mL, 34.41 mmol) dropwise via syringe and stirred for 30 minutes at −78° C. The solution was then treated with a saturated ammonium chloride solution (100 mL), allowed to warm to room temperature, diluted with ether and extracted. The combined organic layers were washed with brine, dried (MgSO4) and concentrated to provide the desired product in quantitative yield. MS (ESI(+)) m/e 196 (M+H)+.

후처리

  1. temperatureto warm to room temperature
  2. extractionextracted
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

출처 및 근거

ORD 기록
ord-3b7925b1660d4f6187f302317a8f9746
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737160B2

반응 노트

불러오는 중…