Butyramide → HCID 15860313, 화합물

HRID 1291713

반응식

HRID 1291713 반응식
[OH:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[CH2:10][C@H:9]2[CH2:11][NH:12][C:13](=[O:17])[CH2:14][CH2:15][CH3:16])[CH:5]=[CH:6][CH:7]=1.[C:18](N)(=O)[CH2:19][CH2:20]C.B(Br)(Br)Br>ClCCl>[CH2:20]([O:1][C:2]1[CH:3]=[C:4]([C@@H:8]2[CH2:10][C@H:9]2[CH2:11][NH:12][C:13](=[O:17])[CH2:14][CH2:15][CH3:16])[CH:5]=[CH:6][CH:7]=1)[CH:19]=[CH2:18]

참가 물질

5

반응물 3

HCID 10927ButyramideHCID 25134Boron tribromideHCID 70274674HCID 70274674, 화합물

생성물 1

HCID 15860313HCID 15860313, 화합물수율 75%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(trans)-N-[[2-(3-Hydroxyphenyl)cyclopropyl]methyl] butanamide: To a stirred solution of (trans)-N-[f2-(3-methoxyphenyl)cyclopropyl]methyl]butanamide (3.50 g, 14.2 mmol) in dichloromethane (50 mL) at -78° C. was added BBr3 (28.4 mL, 1N in CH2Cl2, 28.4 mmol) dropwise. After addition was complete, the cooling bath was removed and stirring was continued for 18 h. The solution was poured over ice/H2O (100 mL) and extracted with 2.5N NaOH. The basic extracts were combined, washed with dichloromethane, and acidified (conc. HCl). The acidic solution was extracted with dichloromethane, the organics were combined, washed with brine, dried (MgSO4), and concentrated to afford 2.49 g (75%) of the title compound: 1H NMR (300 MHz, DMSO-d6)δ0.72-0.84 (m, 5H), 1.09-1.15 (m, 1H), 1.42-1.54 (m, 2H), 1.63-1.69 (m, 1H), 2.02 (t, J=5.0 Hz, 2H), 2.99-3.11 (m, 2H), 6.39-6.50 (m, 3H), 6.98 (t, J=7.8 Hz, 1H), 7.91 (s, 1H), 9.19 (br s, 1H); IR (NaCl Film) 3300, 2964, 1642, 1585, 1542, 1466 cm-1 ; MS (isobutane--DCI) m/e 233; Analysis calc'd for C14H19NO2.0.1 H2O: C, 71.52; H, 8.23; N, 5.96; found: C, 71.53; H, 8.32; N, 5.92.

후처리

  1. additionAfter addition
  2. customthe cooling bath was removed
  3. additionThe solution was poured over ice/H2O (100 mL)
  4. extractionextracted with 2.5N NaOH
  5. washwashed with dichloromethane
  6. extractionThe acidic solution was extracted with dichloromethane
  7. washwashed with brine
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-b1974e77f6e847a4853d0f642cf43c01
출처 데이터셋
uspto-grants-1998_05
특허 번호
US05753709

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