Hydrochloric Acid → tert-Butyl ((1R,2S)-1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1-hydroxypropan-2-yl)carbamate

HRID 1661476노트

반응식

HRID 1661476 반응식
C([Mg]Cl)(C)C.CON(C)[C:9](=[O:20])[C@@H:10]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH3:11].[O:22]1[CH2:27][CH2:26][O:25][C:24]2[CH:28]=[C:29]([Mg]Br)[CH:30]=[CH:31][C:23]1=2.Cl>C1COCC1.O>[O:22]1[C:23]2[CH:31]=[CH:30][C:29]([C@@H:9]([OH:20])[C@@H:10]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:17])[CH3:18])[CH3:11])=[CH:28][C:24]=2[O:25][CH2:26][CH2:27]1

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 11806530(S)-tert-Butyl (1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamateHCID 178418918HCID 178418918, 화합물HCID 178419614HCID 178419614, 화합물

생성물 1

HCID 59339843tert-Butyl ((1R,2S)-1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-1-hydroxypropan-2-yl)carbamate

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매3회

실험 절차

Isopropylmagnesium chloride, 2M in THF (6.5 mL, 13.00 mmol) was added to a suspension of (S)-tert-butyl 1-(methoxy(methyl)amino)-1-oxopropan-2-ylcarbamate (3 g, 12.92 mmol) in THF (30 mL) keeping the temperature below −10° C. (2,3-dihydrobenzo[b][1,4]dioxin-6-yl)magnesium bromide, 0.7M in THF (20 mL, 14.00 mmol) was added. The reaction mixture was stirred at room temperature for 17 hours. 1N HCl (300 mL) was cooled on ice bath to +10° C., the reaction mixture was poured into the acidic water solution and extracted with TBME=tert-butyl methyl ether. The ether phases were washed with water, brine and dried (Na2SO4). Filtration and evaporation of solvents afforded a crude product as a slightly yellow oil that was purified by flash chromatography using TBME:Heptane=1:2 as eluent.

후처리

  1. additionwas added
  2. extractionextracted with TBME=tert-butyl methyl ether
  3. washThe ether phases were washed with water, brine
  4. dry with materialdried (Na2SO4)
  5. filtrationFiltration and evaporation of solvents

출처 및 근거

ORD 기록
ord-16426c6fdbd54b418a1d6862a765074e
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08030340B2

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