Di-tert-butyl dicarbonate → tert-butyl 7-nitro-2,3,4,5-tetrahydro-1H-3-benzazepine-3-carboxylate

HRID 1668580Notes

Reaction equation

HRID 1668580 reaction equation
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]2[CH2:8][CH2:9][NH:10][CH2:11][CH2:12][C:6]=2[CH:5]=1)([O-:3])=[O:2].[O:15](C(OC(C)(C)C)=O)[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[N+:1]([C:4]1[CH:14]=[CH:13][C:7]2[CH2:8][CH2:9][N:10]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:15])[CH2:11][CH2:12][C:6]=2[CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 90495Di-tert-butyl dicarbonateHCID 113100427-Nitro-2,3,4,5-tetrahydro-1H-benzo[D]azepine

Product 1

HCID 21918821tert-butyl 7-nitro-2,3,4,5-tetrahydro-1H-3-benzazepine-3-carboxylateYield 91.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 7-nitro-2,3,4,5-tetrahydro-1H-3-benzazepine (2.33 g) in dry DCM (120 ml, TEA (4.2 ml 2.5 eq), BOC2O (6.1 g, 2.3 eq.), DMAP (296 mg, 0.2 eq.) were added. The mixture was stirred at rt. for 1 h then the solvent was evaporated in vacuo. The material thus obtained was purified by flash chromatography over silica gel (eluting with 20% ethyl acetate in hexane) to give the title compound (3.25 g).

Workup

  1. customthe solvent was evaporated in vacuo
  2. customThe material thus obtained
  3. customwas purified by flash chromatography over silica gel (eluting with 20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-60a14de9775f475e9bb7329c08d493f9
Source dataset
uspto-grants-2011_08
Patent number
US07989444B2

Reaction notes

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