Butyramide → HCID 15860313, compound

HRID 1291713

Reaction equation

HRID 1291713 reaction equation
[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]

Participants

5

Reactant 3

HCID 10927ButyramideHCID 25134Boron tribromideHCID 70274674HCID 70274674, compound

Product 1

HCID 15860313HCID 15860313, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(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.

Workup

  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

Sources & evidence

ORD record
ord-b1974e77f6e847a4853d0f642cf43c01
Source dataset
uspto-grants-1998_05
Patent number
US05753709

Linked notes

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