Acetic Acid → HCID 54188068、化合物

HRID 1637085ノート

反応式

HRID 1637085 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:15])[CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C(O)(=O)C.[C:20]([O:24][C:25]([NH:27][C@@H:28]1[CH2:32][CH2:31][NH:30][CH2:29]1)=[O:26])([CH3:23])([CH3:22])[CH3:21].C([BH3-])#N.[Na+]>CO.CC(O)C.C(OCC)(=O)C>[C:20]([O:24][C:25]([NH:27][C@@H:28]1[CH2:32][CH2:31][N:30]([CH:11]2[CH2:12][CH2:13][C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)([OH:15])[CH2:9][CH2:10]2)[CH2:29]1)=[O:26])([CH3:23])([CH3:21])[CH3:22]

参加物

7

反応物 4

HCID 176Acetic AcidHCID 1514397(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 5003444Sodium cyanoborohydrideHCID 223953644-(4-Fluorophenyl)-4-hydroxycyclohexan-1-one

生成物 1

HCID 54188068HCID 54188068、化合物収率 56%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 22055037Isopropanol ethyl acetate溶媒

実験手順

To a solution of 4-(4-Fluorophenyl)-4-hydroxy-cyclohexanone (2.0 g, 9.6 mmol) and acetic acid (2.6 ml, 48 mmol) in methanol (60 ml) was added (3R)-(+)-3-(tert-butoxycarbonylamino) pyrrolidine (2.6 g, 14.4 mmol). After stirring for 2 hours at room temperature, sodium cyanoborohydride (1M in tetrahydrofuran, 14.4 ml, 14.4 mmol) was added dropwise. The reaction mixture was stirred for 45 minutes, concentrated, diluted with 10% potassium hydrogen sulfate and extracted twice with ether. The aqueous solution was basified with 1N sodium hydroxide and extracted with ethyl acetate three times. Washing with brine, drying and solvent evaporation gave an oil. Flash chromatography (silica gel, 2-propanol-ethyl acetate, 4:96 increasing to 8:92) gave 4-(3-(3R)-tert-Butoxycarbonylamino-pyrrolidin-1-yl)-1-(4-fluorophenyl)-cyclohexanol (2.0 g, 56%); 1H NMR (CDCl3)δ 7.46(m, 2H), 7.02 (m, 2H), 4.89 (m, 1H), 4.18 (m, 1H), 2.94 (m, 1H), 2.71 (m, 2H), 2.42 (m, 1H), 2.26 (m, 1H), 2.13 (m, 1H), 1.83 (m, 9H), 1.63 (m, 1H), 1.44 (s, 9H),

後処理

  1. stirringThe reaction mixture was stirred for 45 minutes
  2. concentrationconcentrated
  3. additiondiluted with 10% potassium hydrogen sulfate
  4. extractionextracted twice with ether
  5. extractionextracted with ethyl acetate three times
  6. washWashing with brine
  7. customdrying
  8. customsolvent evaporation
  9. customgave an oil

出典と根拠

ORDレコード
ord-683fb28eec934c19a8f7fb53f53c755b
出典データセット
uspto-grants-2000_03
特許番号
US06037354

反応ノート

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