Tetrabutylammonium Fluoride → HCID 67311574, 화합물

HRID 1505291

반응식

HRID 1505291 반응식
[Si]([O:18][CH2:19][CH2:20]/[CH:21]=[CH:22]/[C@@H:23]([NH:28][P:29]([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:30])[CH2:24][CH:25]([CH3:27])[CH3:26])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:18][CH2:19][CH2:20]/[CH:21]=[CH:22]/[C@@H:23]([NH:28][P:29]([C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1)([C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)=[O:30])[CH2:24][CH:25]([CH3:26])[CH3:27]

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium Fluoride2회HCID 67310501(S,E)-N-(8-(tert-Butyldiphenylsilyloxy)-2-methyloct-5-en-4-yl)-P,P-diphenylphosphinic amide

생성물 1

HCID 67311574HCID 67311574, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of the TBDPS-protected alcohol 8c (700 mg, 0.983 mmol, crude) in dry THF (8 mL) at 0° C. was added TBAF (1.0M/THE, 1.23 mL, 1.23 mmol), and the reaction mixture was allowed to warm to rt while stirring under argon. As completion was not reached after 4 h, 0.75 eq of TBAF (0.75 mL) was added at 0° C. The reaction mixture was stirred further at rt for 3 h, then quenched with sat. aq. NH4Cl and diluted with EtOAc. The aqueous phase was separated and extracted with EtOAc. The combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated in vacuo. Flash chromatography (SiO2, 95:5, EtOAc/MeOH) afforded 272 mg (77%, 2 steps) of the title compound as a white solid. mp 124.0-124.2° C.; [α]D23-12.1 (c 1.0, DCM); 1H NMR (300 MHz, CDCl3) δ 8.00-7.83 (m, 4 H), 7.58-7.35 (m, 6 H), 5.52 (dd, 1 H, J=15.3, 9.0 Hz), 5.24 (m, 1 H), 4.58 (bs, 1H), 3.78-3.47 (m, 3 H), 2.80 (appdd, 1 H, J=9.2, 3.8 Hz), 2.16 (m, 2 H), 1.68 (bs, 1 H), 1.55-1.43 (m, 1 H), 1.43-1.31 (m, 1 H), 0.87 (dd, 6 H, J=8.6, 6.4 Hz); HRMS (ESI) m/z calcd for C21H28NO2PNa 380.1755. found 380.1725.

후처리

  1. customat 0° C.
  2. stirringThe reaction mixture was stirred further at rt for 3 h
  3. customquenched with sat. aq. NH4Cl
  4. additiondiluted with EtOAc
  5. customThe aqueous phase was separated
  6. extractionextracted with EtOAc
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-3fa2f2579a3148eea8c232bc652b67d3
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09216976B2

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