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

HRID 82762

反応式

HRID 82762 の反応式
[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

参加物

8

反応物 5

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

生成物 1

HCID 2776358(4-Benzylmorpholin-2-yl)methanol収率 64%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
2.5 °C

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-37db046a350a441399b0ff68a327bdd5
出典データセット
uspto-grants-2014_09
特許番号
US08846730B2

関連ノート

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