4-Methylmorpholine → (S)-methyl 4-(tert-butoxycarbonylamino)-5-hydroxypentanoate

HRID 421590ノート

反応式

HRID 421590 の反応式
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.ClC(OCC)=O.[BH4-].[Na+]>C1COCC1>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:10][OH:11])[CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[O:7])([CH3:3])([CH3:2])[CH3:4]

参加物

6

反応物 4

HCID 79724-MethylmorpholineHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydrideHCID 7018756(S)-2-((tert-butoxycarbonyl)amino)-5-methoxy-5-oxopentanoic acid

生成物 1

HCID 11107667(S)-methyl 4-(tert-butoxycarbonylamino)-5-hydroxypentanoate収率 61%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-10 °C

実験手順

In a round-bottom flask, (2S)-2-[(tert-butoxy)carbonylamino]-4-(methoxycarbonyl)butanoic acid (78 mmol, 20.36 g) was dissolved in THF (300 mL). The solution was cooled to −10° C. and N-methylmorpholine (78 mmol, 8.58 mL) and ethyl chloroformate (78 mmol, 7.48 mL) were added, followed by sodium borohydride (234 mmol, 8.85 g). The reaction was stirred for 30 min at this temperature and then quenched by slow addition of saturated solution of ammonium chloride until no further evolution of hydrogen was observed. The reaction mixture was then extracted with ethyl acetate and dried over magnesium sulfate. After filtration, solvent was evaporated and the crude material was purified by column chromatography (SiO2, 1:1 n-hexanes/ethyl acetate) to yield the title compound (11.68 g, 61% yield). ES-MS: 248 (M+1).

後処理

  1. customquenched by slow addition of saturated solution of ammonium chloride until no further evolution of hydrogen
  2. extractionThe reaction mixture was then extracted with ethyl acetate
  3. dry with materialdried over magnesium sulfate
  4. filtrationAfter filtration, solvent
  5. customwas evaporated
  6. customthe crude material was purified by column chromatography (SiO2, 1:1 n-hexanes/ethyl acetate)

出典と根拠

ORDレコード
ord-8333a9c7b08a4f16886717228d2c2c8d
出典データセット
uspto-grants-2012_01
特許番号
US08101588B2

反応ノート

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