3-Pyrrolidone, 1-methyl- → 1-Methyl-3-[(triisopropylsilanyl)-ethynyl]-pyrrolidin-3-ol

HRID 575064

반응식

HRID 575064 반응식
[C:1]([Si:3]([CH:10]([CH3:12])[CH3:11])([CH:7]([CH3:9])[CH3:8])[CH:4]([CH3:6])[CH3:5])#[CH:2].[Li]CCCC.[CH3:18][N:19]1[CH2:23][CH2:22][C:21](=[O:24])[CH2:20]1>O1CCCC1.CCOC(C)=O>[CH3:18][N:19]1[CH2:23][CH2:22][C:21]([C:2]#[C:1][Si:3]([CH:7]([CH3:9])[CH3:8])([CH:4]([CH3:6])[CH3:5])[CH:10]([CH3:12])[CH3:11])([OH:24])[CH2:20]1

참가 물질

6

반응물 3

HCID 1442833-Pyrrolidone, 1-methyl-HCID 2734682(Triisopropylsilyl)acetyleneHCID 178418339Butyllithium

생성물 1

HCID 866930941-Methyl-3-[(triisopropylsilanyl)-ethynyl]-pyrrolidin-3-ol수율 39.1%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

This compound was prepared according to a procedure similar to that described in Procedure B. Into a solution of Ethynyl-triisopropyl-silane (1.1 g, 6 mmol) in tetrahydrofuran (10 mL) was dropped in n-BuLi (2.4 mL, 6 mmol) at −78° C. The solution was stirred for 0.5 h. Then 1-Methyl-pyrrolidin-3-one (0.5 g, 5 mmol) was added. The solution was allowed to warm up to room temperature and stirred for 3 h. Then the reaction mixture was added in 50 mL EtOAc and washed with water three times. The solvent was removed under vacuum to afford 1-Methyl-3-[(triisopropylsilanyl)-ethynyl]-pyrrolidin-3-ol (0.55 g, 39%). 1H NMR (DMSO-d6, 400 MHz): δ 5.53 (s, 1H), 2.74-2.63 (m, 2H), 2.46-2.44 (m, 1H), 2.23 (s, 3H), 2.13-1.96 (m, 2H), 1.07-0.97 (m, 21H). A solution of 1-Methyl-3-[(triisopropylsilanyl)-ethynyl]-pyrrolidin-3-ol (1.0 g, 3.6 mmol) in tetrahydrofuran (10 mL) was treated with Tetrabutyl-ammonium fluoride (0.94 g, 3.6 mmol). The solution was stirred overnight at room temperature. Then the reaction mixture was purified by column (eluent: CH2Cl2: MeOH=10:1) to afford 3-Ethynyl-1-methyl-pyrrolidin-3-ol (0.26 g, 58%). 1H NMR (DMSO-d6, 400 MHz): δ 5.55 (s, 1H), 3.31 (s, 1H), 2.74-2.56 (m, 3H), 2.49-2.46 (m, 1H), 2.22 (s, 3H), 2.11-1.91 (m, 2H).

후처리

  1. customThis compound was prepared
  2. stirringstirred for 3 h
  3. washwashed with water three times
  4. customThe solvent was removed under vacuum

출처 및 근거

ORD 기록
ord-cbe066ff5de04d268cd81dc920819086
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09034866B2

연결된 노트

불러오는 중…