Acetic Acid → HCID 59027969, compound

HRID 714534Notes

Reaction equation

HRID 714534 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][C:11](=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:16]1([C@H:22]([NH2:24])[CH3:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(O)(=O)C>C1COCC1>[C:16]1([C@H:22]([NH:24][CH:11]2[CH2:12][CH2:13][CH2:14][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10]2)[CH3:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6431891-Phenethylamine, (+)-HCID 1512679N-Boc-hexahydro-1H-azepin-4-one

Product 1

HCID 59027969HCID 59027969, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-oxoazepane-1-carboxylic acid tert-butyl ester (90 g, 422 mmol) and (R)-1-phenylethanamine (56.4 g, 465 mmol) in THF (1000 mL) was stirred at rt for 15 min and STAB (107.4 g, 510 mmol) was added. The mixture was cooled to 0° C. in an ice bath, then acetic acid (26.7 g, 450 mmol) was added. The mixture was stirred overnight at rt then concentrated in vacuo, residue dissolved in DCM (800 mL) and washed with sat. NaHCO3 sol. (2×300 mL), dried (Na2SO4). The solvents were removed in vacuo, and the residue was purified by column chromatography (gradient 0% to 3% MeOH in DCM) to give tert-butyl 4-{[(1R)-1-phenylethyl]amino}azepane-1-carboxylate (90 g, 67.0%) as a mixture of two diastereoisomers.

Workup

  1. additionSTAB (107.4 g, 510 mmol) was added
  2. temperatureThe mixture was cooled to 0° C. in an ice bath
  3. stirringThe mixture was stirred overnight at rt
  4. concentrationthen concentrated in vacuo, residue
  5. dissolutiondissolved in DCM (800 mL)
  6. washwashed with sat. NaHCO3 sol. (2×300 mL)
  7. dry with materialdried (Na2SO4)
  8. customThe solvents were removed in vacuo
  9. customthe residue was purified by column chromatography (gradient 0% to 3% MeOH in DCM)

Sources & evidence

ORD record
ord-f143a868959f4e1faf5942f8aa7917ef
Source dataset
uspto-grants-2015_11
Patent number
US09187451B2

Reaction notes

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