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

HRID 870936ノート

反応式

HRID 870936 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 84.1%

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 a nitrogen atmosphere was added N-methylmorpholine (0.223 ml, 2.028 mmol) followed by isobutyl chloroformate (0.266 ml, 2.028 mmol) dropwise and stirred for 30 min. The reaction mixture was filtered. The filtrate was added to sodium borohydride (147 mg, 3.87 mmol) in water (10 mL) and stirred for 5 min. The mixture was 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, 1.55 mmol, 84% yield) as a white solid which was taken to the next step without any purification. 1H NMR (400 MHz, CDCl3) δ 3.73-3.59 (m, 3H), 2.24-2.16 (m, 2H), 1.87-1.69 (m, 2H), 1.44 (s, 9H).

後処理

  1. filtrationThe reaction mixture was 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-ac49585f5b50427bb99e1e975351259b
出典データセット
uspto-grants-2015_03
特許番号
US08969564B2

反応ノート

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