홈MCP워크벤치Skills
홈워크벤치알림마이페이지
llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
  1. 홈
  2. /반응

tert-Butyl methyl ether → (S)-1-{(3aS,7E,7aR)-7-(bromomethylene)-3a,4,5,6,7,7a-hexahydro-3a-methyl-1H-indene-3-yl}ethanol

HRID 1922640
노트
인쇄 미리보기

반응식

HRID 1922640 반응식
[CH3:1]OC(C)(C)C.C[Zn]C.[Br:10]/[CH:11]=[C:12]1/[C@H:13]2[C@:17]([CH3:21])([CH2:18][CH2:19][CH2:20]/1)[C:16]([CH:22]=[O:23])=[CH:15][CH2:14]2>C(O[Ti](OC(C)C)(OC(C)C)OC(C)C)(C)C.[C@@H]1(NS(C(F)(F)F)(=O)=O)CCCC[C@H]1NS(C(F)(F)F)(=O)=O.C(OCC)(=O)C>[Br:10]/[CH:11]=[C:12]1\[CH2:20][CH2:19][CH2:18][C@@:17]2([CH3:21])[C@H:13]\1[CH2:14][CH:15]=[C:16]2[C@@H:22]([OH:23])[CH3:1]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

HCID 15413tert-Butyl methyl etherHCID 59456515(3aR,4E,7aS)-4-(bromomethylene)-3a,4,5,6,7,7a-hexahydro-7a-methyl-3H-indene-1-carbaldehyde2회HCID 178477796HCID 178477796, 화합물

생성물 1

HCID 59456520(S)-1-{(3aS,7E,7aR)-7-(bromomethylene)-3a,4,5,6,7,7a-hexahydro-3a-methyl-1H-indene-3-yl}ethanol수율 100%

시약·촉매·용매 3

HCID 11090167
(1R)-trans-N,N'-1,2-Cyclohexanediylbis(1,1,1-trifluoromethanesulfonamide)
촉매
HCID 178460666HCID 178460666, 화합물촉매
HCID 8857Ethyl Acetate용매

반응 조건

온도
50 °C

실험 절차

(1R)-trans-N,N′-1,2-cyclohexanediylbis(1,1,1-trifluoromethanesulfonamide) (2.3 mg, 0.006 mmol) was placed in a reaction vessel. After replacing the atmosphere with nitrogen, t-butyl methyl ether (0.03 ml) was added thereto and dissolved. To the solution, tetraisopropoxy titanium (0.0177 ml, 0.06 mmol) was added at room temperature, and the resulting mixture was heated at 50° C. for 30 minutes. After cooling to room temperature, dimethylzinc (1.0 M in heptane, 0.12 ml, 0.12 mmol) was added thereto. The obtained reaction mixture was added to (3aR,4E,7aS)-4-(bromomethylene)-3a,4,5,6,7,7a-hexahydro-7a-methyl-3H-indene-1-carbaldehyde (Compound 29: 15.3 mg, 0.06 mmol). After stirring the reaction solution at room temperature for 1 hour, ethyl acetate (30 ml) was added thereto, and the resulting mixture was washed with 2N hydrochloric acid, saturated brine and with saturated aqueous sodium hydrogen carbonate solution, respectively. The organic layer was dried over sodium sulfate, and the solvent was evaporated to obtain the reaction mixture. The reaction mixture was purified by preparative TCL to obtain (S)-1-{(3aS,7E,7aR)-7-(bromomethylene)-3a,4,5,6,7,7a-hexahydro-3a-methyl-1H-indene-3-yl}ethanol (18.4 mg, 100%). The spectrum data thereof agreed with the data described in Example 4.

후처리

  1. additionwas added
  2. dissolutiondissolved
  3. temperatureAfter cooling to room temperature
  4. customThe obtained reaction mixture
  5. washthe resulting mixture was washed with 2N hydrochloric acid, saturated brine and with saturated aqueous sodium hydrogen carbonate solution
  6. dry with materialThe organic layer was dried over sodium sulfate
  7. customthe solvent was evaporated
  8. customto obtain the reaction mixture
  9. customThe reaction mixture was purified by preparative TCL

출처 및 근거

ORD 기록
ord-3695cd263fa04fa5bcbd7f6e0258f1a9
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08173824B2

반응 노트

불러오는 중…

이 페이지에서참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트