Acetic Acid → HCID 54188068, 화합물

HRID 1637085노트

반응식

HRID 1637085 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 54188068HCID 54188068, 화합물수율 56%

시약·촉매·용매 2

HCID 887Methanol용매HCID 22055037Isopropanol ethyl acetate용매

실험 절차

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),

후처리

  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

출처 및 근거

ORD 기록
ord-683fb28eec934c19a8f7fb53f53c755b
출처 데이터셋
uspto-grants-2000_03
특허 번호
US06037354

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