Borane → HCID 178419237, 화합물

HRID 258137

반응식

HRID 258137 반응식
[C:1]1([C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C@@H:9]2[CH2:13][CH2:12][CH2:11][NH:10]2)[OH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CSC.[BH3:23].B>C1(C)C=CC=CC=1>[C:1]1([C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([CH:9]2[CH2:13][CH2:12][CH2:11][NH:10]2)[OH:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1.[BH3:23]

참가 물질

5

반응물 3

HCID 6331BoraneHCID 27248992-Pyrrolidinemethanol, alpha,alpha-diphenyl-, (S)-HCID 12423031(Dimethyl sulfide)trihydroboron

생성물 1

HCID 178419237HCID 178419237, 화합물

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
20 °C

실험 절차

A 250-mL three-necked flask fitted with a mechanical stirrer, nitrogen inlet tube, and teflon coated thermocouple probe, was charged with a solution of the free base product of Example 1 Step B (20.7 g, 81.7 mmol) in dry toluene (100 mL). To the stirred solution at 20° C. was added borane-dimethyl sulfide (10M, 10.0 mL, 100 mmol) over 5 minutes via syringe. The borane reacted immediately in an exothermic reaction (raising the internal temperature from 20° C. to 32° C.) forming a thick white precipitate. With continued stirring, the mixture was allowed to cool to room temperature (20° C.) over a 1 hour period. The mixture was filtered, and the product cake washed with dry toluene (25 mL). The product was dried in vacuo (20° C., 0.01 mBar) to constant weight. Yield 15.7 g (72%) of a white crystal line solid. m.p. 130°-132° C. (dec). 1H NMR (CDCl3 ) δ7.7-7.1 (m, 10 H, Ar-H), 5.15 (s, 1 H, --OH), 4.5 (br, 1 H, --NH), 4.2 (m, 1 H, C2-H), 3.25 (m, 2 H, C5-H2), 2.6 (m, 1 H, C4- H), 2.3 (m, 1 H, C4-H), 1.85 (m, 1 H, C3-H), 1.6 (m, 1 H, C3-H), 2.1-0.7 (br, 3 H, BH3). 13C NMR (CDCl3) δ145.8, 144.5 (C1', C1"), 129.1, 128.2 (C3', C5', C3", C5"), 127.4, 127.0 (C4', C4"), 125.2, 125.1 (C2', C6', C2", C6"), 76.5 (Cα), 69.6 (C2), 55.6 (C 5), 20.6 (C4), 19.9 (C3).

후처리

  1. customA 250-mL three-necked flask fitted with a mechanical stirrer, nitrogen inlet tube
  2. temperatureraising the internal temperature from 20° C. to 32° C.)
  3. customforming a thick white precipitate
  4. filtrationThe mixture was filtered
  5. washthe product cake washed with dry toluene (25 mL)
  6. customThe product was dried in vacuo (20° C., 0.01 mBar) to constant weight

출처 및 근거

ORD 기록
ord-969b93af375048c4b3dc8543aaf96b43
출처 데이터셋
uspto-grants-1993_11
특허 번호
US05264585

연결된 노트

불러오는 중…