4-Methylmorpholine → Tert-butyl (5,5,5-trifluoro-1-hydroxypentan-2-yl)carbamate

HRID 1398331ノート

反応式

HRID 1398331 の反応式
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:13][CH2:14][C:15]([F:18])([F:17])[F:16])[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.ClC(OCC(C)C)=O.[BH4-].[Na+]>C1COCC1.O.C(OCC)(=O)C>[F:16][C:15]([F:17])([F:18])[CH2:14][CH2:13][CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH2:10][OH:11]

参加物

8

反応物 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 4311764Sodium borohydrideHCID 534019302-((Tert-butoxycarbonyl)amino)-5,5,5-trifluoropentanoic acid

生成物 1

HCID 86710332Tert-butyl (5,5,5-trifluoro-1-hydroxypentan-2-yl)carbamate収率 84.4%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a stirred solution of 2-((tert-butoxycarbonyl)amino)-5,5,5-trifluoropentanoic acid (500 mg, 1.843 mmol) in THF (15 mL) cooled to −10° C. under nitrogen atmosphere was added N-methylmorphline (0.223 mL, 2.028 mmol) followed by isobutyl chloroformate (0.266 mL, 2.028 mmol) dropwise. The solution was then stirred for 30 min then filtered. The filtrate was added to sodium borohydride (147 mg, 3.87 mmol) in water (10 mL), stirred for 5 min and diluted with ethyl acetate (10 mL). The organic layer was separated and washed with brine (2×10 mL), dried (Na2SO4) and evaporated under reduced pressure to afford tert-butyl (5,5,5-trifluoro-1-hydroxypentan-2-yl)carbamate (400 mg, 1.555 mmol, 84% yield) as a white solid which was taken to the next step without further purification. 1H NMR (400 MHz, MeOD) δ 3.44-3.56 (m, 3H), 2.16-2.26 (m, 2H), 1.83-1.92 (m, 1H), 1.57-1.67 (m, 1H), 1.47 (s, 9H).

後処理

  1. filtrationthen filtered
  2. stirringstirred for 5 min
  3. customThe organic layer was separated
  4. washwashed with brine (2×10 mL)
  5. dry with materialdried (Na2SO4)
  6. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-7064ee34b629441d8a8037c1cf821aad
出典データセット
uspto-grants-2014_12
特許番号
US08901305B2

反応ノート

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