(3-bromoprop-1-en-2-yl)benzene → HCID 67440613, 화합물

HRID 1664784노트

반응식

HRID 1664784 반응식
[CH3:1][O:2][C:3](=[O:21])[CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:7][CH2:6]1.Br[CH2:23][C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[CH2:25]>O1CCCC1>[CH3:1][O:2][C:3]([CH:4]([CH:5]1[CH2:6][CH2:7][N:8]([C:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:12])[CH2:9][CH2:10]1)[CH2:25][C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[CH2:23])=[O:21]

참가 물질

4

반응물 2

HCID 234998(3-bromoprop-1-en-2-yl)benzeneHCID 40429392Benzyl 4-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate

생성물 1

HCID 67440613HCID 67440613, 화합물수율 77.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Lithium hexamethyldisilylazide (1.0 M in THF; 7.31 mL, 7.31 mmol) was added to solution of benzyl 4-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate (1.94 g, 6.65 mmol) in tetrahydrofuran (35 mL) at −78° C. After 40 min, [1-(bromomethyl)vinyl]benzene (1.08 mL, 7.31 mmol) was added and the reaction mixture was warmed to ambient temperature. After 18 h, the mixture was quenched with saturated aqueous ammonium chloride and extracted with ethyl acetate (2×). The combined organic extracts were dried over magnesium sulfate, filtered and concentrated. Purification by silica gel chromatography (100% hexanes→40% hexanes/ethyl acetate) gave the title compound (2.11 g). MS 408.2 (M+1).

후처리

  1. waitAfter 18 h
  2. customthe mixture was quenched with saturated aqueous ammonium chloride
  3. extractionextracted with ethyl acetate (2×)
  4. dry with materialThe combined organic extracts were dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica gel chromatography (100% hexanes→40% hexanes/ethyl acetate)

출처 및 근거

ORD 기록
ord-6c8b49e2620d4dc5809317fc8a456a3e
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08039460B2

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