tert-Butyldimethylsilyl chloride → 1-(Prop-2-enyl)-3-(r)-(t-butyldimethylsilyloxymethyl)-4-(s)-(3-thienyl)pyrrolidine

HRID 1386734노트

반응식

HRID 1386734 반응식
[CH2:1]([N:4]1[CH2:8][C@H:7]([C:9]2[CH:13]=[CH:12][S:11][CH:10]=2)[C@@H:6]([CH2:14][OH:15])[CH2:5]1)[CH:2]=[CH2:3].CCN(C(C)C)C(C)C.[C:25]([Si:29](Cl)([CH3:31])[CH3:30])([CH3:28])([CH3:27])[CH3:26]>C(Cl)Cl>[CH2:1]([N:4]1[CH2:8][C@H:7]([C:9]2[CH:13]=[CH:12][S:11][CH:10]=2)[C@@H:6]([CH2:14][O:15][Si:29]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:31])[CH3:30])[CH2:5]1)[CH:2]=[CH2:3]

참가 물질

5

반응물 3

HCID 28928tert-Butyldimethylsilyl chlorideHCID 81531DiisopropylethylamineHCID 213410491-(Prop-2-enyl)-3-(r)-(hydroxymethyl)-4-(s)-(3-thienyl)pyrrolidine

생성물 1

HCID 213410501-(Prop-2-enyl)-3-(r)-(t-butyldimethylsilyloxymethyl)-4-(s)-(3-thienyl)pyrrolidine수율 77.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of 1.06 g (4.75 mmol) of 1-(prop-2-enyl)(3-(R)-(hydroxymethyl))-4-(S)-(3-thienyl)pyrrolidine (from EXAMPLE 87, Step A) in 12.0 mL of CH2Cl2 at 0° C. was treated with 0.99 mL (5.7 mmol) of DIEA and 855 mg (5.6 mmol) of t-butyldimethyl silyl chloride. After warming to rt and stirring for 20 h, the solution was partitioned between 100 mL of ether and 100 mL of H2O. After separating the phases, the aqueous layer was extracted with 100 mL of ether. The combined organic phases were dried over MgSO4 and concentrated. The residue was purified by flash chromatography eluting with 3:1 v/v hexanes/EtOAc to yield 1.24 g (77%) of the title compound: RF: 0.54 (3:2 v/v hexanes/EtOAc); 1H NMR (300 MHz) δ 0.0 (s, 6H), 0.86 (s, 9H), 2.35 (m, 1H), 2.52-2.71 (m, 3H), 2.97-3.20 (m, 4H), 3.54-3.66 (m, 2H), 5.06-5.21 (m, 2H), 5.89 (m, 1H). 6.98-7.02 (m, 2H), 7.22 (m, 1H).

후처리

  1. customthe solution was partitioned between 100 mL of ether and 100 mL of H2O
  2. customAfter separating the phases
  3. extractionthe aqueous layer was extracted with 100 mL of ether
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography
  7. washeluting with 3:1 v/v hexanes/EtOAc

출처 및 근거

ORD 기록
ord-c0ffabef90314d6886f7453639b0dad5
출처 데이터셋
uspto-grants-2001_07
특허 번호
US06265434B1

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