Citric Acid → (4-Benzylmorpholin-2-yl)methanol

HRID 82762

반응식

HRID 82762 반응식
[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([C:14](O)=[O:15])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.C(Cl)(=O)OCC.[BH4-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1.CO>[CH2:1]([N:8]1[CH2:13][CH2:12][O:11][CH:10]([CH2:14][OH:15])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

8

반응물 5

HCID 311Citric AcidHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 27763534-Benzylmorpholine-2-carboxylic acidHCID 4311764Sodium borohydride

생성물 1

HCID 2776358(4-Benzylmorpholin-2-yl)methanol수율 64%

시약·촉매·용매 2

HCID 887Methanol용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
2.5 °C

실험 절차

To a solution of 4-benzylmorpholine-2-carboxylic acid (5 g, 22.6 mmol) and triethylamine (3.35 mL, 24 mmol) in THF (100 mL) at −10° C. in a flask equipped with a condenser was added ethyl carbonochloridate (2.5 g, 23 mmol) dropwise and the mixture was stirred at −10° C. to −5° C. for 20 min. Sodium borohydride (2.27 g, 60 mmol) was added followed by methanol (25 mL) from the top of the condenser at such rate to maintain the temperature between 0-5° C. The reaction mixture was allowed to warm to room temperature, acidified to pH 5 with the addition of 10% aqueous citric acid, and concentrated under reduced pressure. The residue was dissolved in EtOAc, washed with water, brine, and dried with MgSO4. Purification of the residue by column chromatography (SiO2, eluted with EtOAc) afforded 3 g of the title compound. MS (DCI/NH3) m/z 208 (M+H)+.

후처리

  1. temperatureto warm to room temperature
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed with water, brine
  5. dry with materialdried with MgSO4
  6. customPurification of the residue
  7. washby column chromatography (SiO2, eluted with EtOAc)

출처 및 근거

ORD 기록
ord-37db046a350a441399b0ff68a327bdd5
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846730B2

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