Lithium Hexamethyldisilazide → Methyl 4-{2-(3-bromophenyl)-3-[(4-methoxybenzyl)oxy]-1-methyl-3-oxopropyl}benzoate

HRID 1880601노트

반응식

HRID 1880601 반응식
[Li+].C[Si]([N-][Si](C)(C)C)(C)C.[Br:11][C:12]1[CH:13]=[C:14]([CH2:18][C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)=[O:20])[CH:15]=[CH:16][CH:17]=1.Br[CH:32]([C:34]1[CH:43]=[CH:42][C:37]([C:38]([O:40][CH3:41])=[O:39])=[CH:36][CH:35]=1)[CH3:33]>C1COCC1>[Br:11][C:12]1[CH:13]=[C:14]([CH:18]([C:19]([O:21][CH2:22][C:23]2[CH:24]=[CH:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=2)=[O:20])[CH:32]([C:34]2[CH:43]=[CH:42][C:37]([C:38]([O:40][CH3:41])=[O:39])=[CH:36][CH:35]=2)[CH3:33])[CH:15]=[CH:16][CH:17]=1

참가 물질

5

반응물 3

HCID 2733832Lithium HexamethyldisilazideHCID 12342351Methyl 4-(1-bromoethyl)benzoateHCID 866195534-Methoxybenzyl (3-bromophenyl)acetate

생성물 1

HCID 67262891Methyl 4-{2-(3-bromophenyl)-3-[(4-methoxybenzyl)oxy]-1-methyl-3-oxopropyl}benzoate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

LHMDS (1.0M THF, 2.6 mL) was added dropwise to a −78° C. THF (4 mL) solution containing the intermediate from Step A (0.827 g, 2.47 mmol). After stirring 10 minutes a THF (4 mL) solution containing methyl 4-(1-bromoethyl)benzoate (0.6 g, 2.47 mmol) was added dropwise. The solution was allowed to warm to room temperature. After 1.5 hours the solution was partitioned between ethyl acetate and aqueous 1N HCl. The organic phase was washed with water, brine and dried over magnesium sulfate. The solution was filtered and the residue purified by silica gel chromatography using a hexanes/ethyl acetate gradient to give the title compounds as a 1.67/1 mixture of diastereomers. 1H NMR (400 MHz, CDCl3): selected data δ 5.16 (d, J=12.0 Hz); 5.01 (d, J=12.0 Hz); 4.82 (d, J=12.0 Hz); 4.64 (d, J=11.9 Hz); 1.34 (d, J=6.8 Hz); 1.02 (d, J=7.0 Hz). Minor diastereomer: LCMS1 4.08 min (N+Na)=519. Major diastereomer: LCMS1 4.19 min (M+Na)=519.

후처리

  1. additionwas added dropwise
  2. customAfter 1.5 hours the solution was partitioned between ethyl acetate and aqueous 1N HCl
  3. washThe organic phase was washed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationThe solution was filtered
  6. customthe residue purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-660ecd5a169f4952aea7f4d8953aa2b1
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318760B2

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