Acetone → HCID 67264073, compound

HRID 1688053Notes

Reaction equation

HRID 1688053 reaction equation
[CH3:1][C:2]([CH3:4])=O.[N+:5]([C:8]1[CH:9]=[CH:10][C:11]2[O:17][CH2:16][CH2:15][CH2:14][NH:13][C:12]=2[CH:18]=1)([O-:7])=[O:6].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(Cl)Cl.C(=O)(O)[O-].[Na+].[Ti](Cl)(Cl)(Cl)Cl>[CH:2]([N:13]1[C:12]2[CH:18]=[C:8]([N+:5]([O-:7])=[O:6])[CH:9]=[CH:10][C:11]=2[O:17][CH2:16][CH2:15][CH2:14]1)([CH3:4])[CH3:1]

Participants

8

Reactant 3

HCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 109871302,3,4,5-Tetrahydro-7-nitro-1,5-benzoxazepine

Product 1

HCID 67264073HCID 67264073, compoundYield 42%

Reagents, catalysts & solvents 4

HCID 24193Titanium TetrachlorideCatalystHCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent2×HCID 516892Sodium BicarbonateSolvent

Procedure

Acetone (0.284 mL, 3.86 mmol) was added to a solution of 2-Nitro-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene (0.250 g, 1.29 mmol) in 1,2-Dichloroethane (5 mL), followed by 1.00 M of Titanium tetrachloride in Methylene chloride (1.29 mL). The reaction mixture was stirred for 2 hours. Then, Sodium triacetoxyborohydride (1.36 g, 6.44 mmol) was added and the reaction was stirred overnight. The reaction mixture was diluted with 30 mL DCM, 30 mL saturated sodium bicarbonate and extracted. The organic layer was then concentrated and purified by column chromatography (ISCO 0-60% EtOAc) to give 9-Isopropyl-2-nitro-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene as orange solids (128 mg, 42%). LCMS: 237; 1H-NMR (DMSO): 7.47 (m, 2H), 6.91 (d, 1H, J=8.5 Hz), 4.31 (m, 2H), 3.86 (sept, 1H, J=6.5 Hz), 3.30 (m, 2H), 1.92 (m, 2H), 1.19 (d, 6H, J=6.5 Hz).

Workup

  1. stirringthe reaction was stirred overnight
  2. extractionextracted
  3. concentrationThe organic layer was then concentrated
  4. custompurified by column chromatography (ISCO 0-60% EtOAc)

Sources & evidence

ORD record
ord-bd0b3ee3678d41ec944dfcc8708b701d
Source dataset
uspto-grants-2012_04
Patent number
US08148391B2

Reaction notes

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