Acetic Acid → HCID 58080614, compound

HRID 2264144

Reaction equation

HRID 2264144 reaction equation
[O:1]1[C:7]2[CH:8]=[CH:9][C:10]([CH:12]=O)=[CH:11][C:6]=2[O: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(Cl)(Cl)Cl>[O:1]1[C:7]2[CH:8]=[CH:9][C:10]([CH2:12][NH:18][CH2:14][CH:15]([CH3:17])[CH3:16])=[CH:11][C:6]=2[O:5][CH2:4][CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 6558IsobutylamineHCID 27763883,4-dihydro-2H-1,5-benzodioxepine-7-carbaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 58080614HCID 58080614, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6212ChloroformSolvent

Procedure

To an ice cold mixture of 15 g of 3,4-dihydro-2H-1,5-benzodioxepine-7-carbaldehyde and 67 mL (8 equiv) of isobutylamine in 100 mL of 1,2-dichloroethane was added 50 mL (10 equiv) of acetic acid and 25 g (1.4 equiv) of sodium triacetoxyborohydride. The mixture was allowed to warm and stir overnight then diluted with 500 mL of chloroform and washed with 500 mL of 5N NaOH. The aqueous layer was extracted with 4 additional 100 mL portions of chloroform and the combined extracts dried over magnesium sulfate and concentrated under reduced pressure. After drying under vacuum the product was obtained as clear oil: MS (m+1)=236.2; 1H NMR (400 MHz, CDCl3) 7.0-6.8 (m, 3H), 4.2 (q, 4H), 3.65 (s, 2H), 2.42 (d, 2H), 2.2 (m, 2H), 1.8 (m, 1H), 0.9 (d, 6H).

Workup

  1. temperatureto warm
  2. washwashed with 500 mL of 5N NaOH
  3. extractionThe aqueous layer was extracted with 4 additional 100 mL portions of chloroform
  4. dry with materialthe combined extracts dried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customAfter drying under vacuum the product
  7. customwas obtained as clear oil

Sources & evidence

ORD record
ord-b4c66c8c1b024f44b971a54ec2f354a6
Source dataset
uspto-grants-2010_12
Patent number
US07855201B2

Linked notes

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