Diisopropylethylamine → 1-Tert-butyl 4-methyl azepane-1,4-dicarboxylate

HRID 1036704Notes

Reaction equation

HRID 1036704 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:14][CH2:13][CH2:12][CH:11]([C:15]([OH:17])=[O:16])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:18]CN(C(C)C)C(C)C.F[B-](F)(F)F.C[O+](C)C>C(Cl)Cl>[N:8]1([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:14][CH2:13][CH2:12][CH:11]([C:15]([O:17][CH3:18])=[O:16])[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)HCID 231606081-[(Tert-butoxy)carbonyl]azepane-4-carboxylic acid

Product 1

HCID 710603801-Tert-butyl 4-methyl azepane-1,4-dicarboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-(tert-Butoxycarbonyl)azepane-4-carboxylic acid (1.0 g; 4.11 mmol) in DCM (20 ml) and treated with DIPEA (1.5 ml, 8.22 mmol) followed by trimethyloxonium tetrafluoroborate (790 mg, 5.34 mmol) in DCM (5 ml). The mixture was stirred at RT for 3 hours and concentrated in vacuo. The residue was partitioned between EtOAc and water. The organic portion was separated and the aqueous was further extracted with EtOAc. The combined organic extracts were washed with brine, dried over MgSO4 and concentrated in vacuo to afford the title compound which was used without further purification.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was partitioned between EtOAc and water
  3. customThe organic portion was separated
  4. extractionthe aqueous was further extracted with EtOAc
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2770b30acaad4a0b9668812cd36361af
Source dataset
uspto-grants-2013_10
Patent number
US08546416B2

Reaction notes

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