Ethyl formate → HCID 86621674, compound

HRID 1364113Notes

Reaction equation

HRID 1364113 reaction equation
[O:1]=[C:2]1[CH2:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4][CH2:3]1.C([N-]C(C)C)(C)C.[Li+].[CH:24](OCC)=[O:25]>O1CCCC1>[CH:24]([CH:8]1[C:2](=[O:1])[CH2:3][CH2:4][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:6][CH2:7]1)=[O:25]

Participants

5

Reactant 3

HCID 8025Ethyl formateHCID 1512679N-Boc-hexahydro-1H-azepin-4-oneHCID 2724682Lithium diisopropylamide

Product 1

HCID 86621674HCID 86621674, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

1,1-Dimethylethyl 4-oxohexahydro-1H-azepine-1-carboxylate (commercially available from e.g. Magic Chemicals) (2.0 g, 9.4 mmol) in tetrahydrofuran at −78° C. was treated with a 2M solution of lithium diisopropylamide (4.7 ml, 9.4 mmol) in tetrahydrofuran. After 20 minutes neat ethyl formate (0.7 g, 9.4 mmol) was added and the reaction mixture was allowed to warm to room temperature. After 2 hours the reaction was quenched, poured into water and extracted several times with ethyl acetate. The combined organic layers were then dried and reduced in vacuo to furnish the title compound which may be used without further purification (D8).

Workup

  1. customAfter 2 hours the reaction was quenched
  2. additionpoured into water
  3. extractionextracted several times with ethyl acetate
  4. customThe combined organic layers were then dried

Sources & evidence

ORD record
ord-18f6922ba025451d8e4f6bbd1239fed9
Source dataset
uspto-grants-2011_02
Patent number
US07888347B2

Reaction notes

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