Toluene → (S)-5-benzyloxymethylmorpholin-3-one

HRID 16346

반응식

HRID 16346 반응식
Br[CH2:2][C:3](Cl)=[O:4].C1(C)C=CC=CC=1.[OH-].[Na+].[NH2:15][C@@H:16]([CH2:19][O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:17][OH:18]>C1COCC1>[CH2:21]([O:20][CH2:19][C@@H:16]1[NH:15][C:3](=[O:4])[CH2:2][O:18][CH2:17]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

참가 물질

6

반응물 4

HCID 1140Toluene2회HCID 14798Sodium HydroxideHCID 89602Bromoacetyl chlorideHCID 141184082-Amino-3-(benzyloxy)propan-1-ol

생성물 1

HCID 67077731(S)-5-benzyloxymethylmorpholin-3-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
0 °C

실험 절차

Bromoacetyl chloride (5.06 mL) was added to a solution mixture of toluene (100 mL) and a 2 N sodium hydroxide aqueous solution (100 mL) of (R)-(+)-2-amino-3-benzyloxy-1-propanol (10 g) under ice-cooling. The resulting reaction solution was stirred at 0° C. for 30 min and then further stirred at 60° C. for 1 hr. The reaction solution was cooled to room temperature, and a solution mixture of toluene and THF (1:1) was added thereto. The organic layer was separated, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: heptane-ethyl acetate system) to give 1.36 g of the title compound. The physical property values of this compound were as follows:

후처리

  1. customThe resulting reaction solution
  2. stirringfurther stirred at 60° C. for 1 hr
  3. temperatureThe reaction solution was cooled to room temperature
  4. additionwas added
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluting solvent: heptane-ethyl acetate system)

출처 및 근거

ORD 기록
ord-0de979c1ecc44607a3376da65e857d14
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737141B2

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