Acetic Acid → HCID 60209724, compound

HRID 2264167Notes

Reaction equation

HRID 2264167 reaction equation
[O:1]1[C:7]2[CH:8]=[C:9]([CH:12]=O)[CH:10]=[CH:11][C:6]=2[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:14]([NH2:18])[CH:15]([CH3:17])[CH3:16].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(OCC)(=O)C>[CH3:16][CH:15]([CH3:17])[CH2:14][NH:18][CH2:12][C:9]1[CH:10]=[CH:11][C:6]2[CH2:5][CH2:4][CH2:3][CH2:2][O:1][C:7]=2[CH:8]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6558IsobutylamineHCID 5049666Sodium triacetoxyborohydrideHCID 574322742,3,4,5-Tetrahydro-1-benzoxepine-8-carbaldehyde

Product 1

HCID 60209724HCID 60209724, compoundYield 106.3%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 0.48 g (2.7 mmol) of 2,3,4,5-tetrahydro-1-benzoxepine-8-carbaldehyde and 1.33 mL (13.5 mmol, 5 equiv) of isobutylamine in 22 mL of 1,2-dichloroethane was added 0.86 mL (15.0 mmol, 5.5 equiv) of acetic acid. The mixture was stirred under nitrogen at ambient temperature for 20 minutes and 0.64 g (3.0 mmol, 1.1 equiv) of sodium triacetoxyborohydride was added. The mixture was stirred overnight then diluted with 125 mL of ethyl acetate and washed with 60 mL each of saturated sodium bicarbonate solution, water and brine, dried over sodium sulfate, filtered, and concentrated under reduced pressure to give 0.67 g of a yellow oil. Purification by flash chromatography (0-10% methanol in ethyl acetate) gave the product as a colorless oil. MS (m+1)=234.2; 1H NMR (400 MHz, CDCl3) 7.07 (d, 1H, J 8 Hz), 7.09 (d, 1H, J 1.5 Hz), 6.99 (m, 1H), 3.99 (m, 2H), 3.72 (s, 2H), 2.70 (m, 2H), 2.43 (d, 2H, J 7 Hz), 1.95 (m, 2H), 1.77 (m, 1H), 1.71 (m, 2H), 1.5 (br s, 1H), 0.91 (d, 6H, J 7 Hz).

Workup

  1. stirringThe mixture was stirred overnight
  2. washwashed with 60 mL each of saturated sodium bicarbonate solution, water and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-22ed2c6a1ed4459683a0823216e232ff
Source dataset
uspto-grants-2010_12
Patent number
US07855201B2

Reaction notes

Loading…