Boron tribromide → (trans)-N-[[2-[3-(2-Propenyloxy)phenyl]cyclopropyl]methyl]butanamide

HRID 1419951

Reaction equation

HRID 1419951 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.CO[C:20]1[CH:21]=C([C@@H]2C[C@H]2CNC(=O)CCC)C=C[CH:25]=1.B(Br)(Br)Br>ClCCl>[CH2:21]([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:20]=[CH2:25]

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 15860309(trans)-N-[[2-(3-methoxyphenyl)cyclopropyl]methyl]butanamideHCID 70274674HCID 70274674, compound

Product 1

HCID 15860313(trans)-N-[[2-[3-(2-Propenyloxy)phenyl]cyclopropyl]methyl]butanamideYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(trans)-N-[[2-(3-Hydroxyphenyl)cyclopropyl]methyl]butanamide: To a stirred solution of (trans)-N-[[2-(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 2.5 N 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) δ 0.72-0.84 (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 2.5 N 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-76a393d8f83b490e9ba8aacd4ffe6e65
Source dataset
uspto-grants-1999_03
Patent number
US05889031

Linked notes

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