Morpholine → HCID 67264195, compound

HRID 1041694Notes

Reaction equation

HRID 1041694 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH2:7]([N:9]1[C:15]2[CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=[CH:19][C:14]=2[O:13][CH2:12][C:11](=[O:23])[CH2:10]1)[CH3:8].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH2:7]([N:9]1[C:15]2[CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=[CH:19][C:14]=2[O:13][CH2:12][CH:11]([OH:23])[CH2:10]1)[CH3:8].[CH2:7]([N:9]1[C:15]2[CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=[CH:19][C:14]=2[O:13][CH2:12][CH:11]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)[CH2:10]1)[CH3:8]

Participants

6

Reactant 3

HCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 67264326HCID 67264326, compound

Product 2

HCID 67264195HCID 67264195, compoundYield 60%HCID 67264434HCID 67264434, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Morpholine (0.10 mL, 1.1 mmol) and 9-Ethyl-2-nitro-8,9-dihydro-5-oxa-9-aza-benzocyclohepten-7-one (74 mg, 0.31 mmol) in Methylene chloride (5 mL) was stirred for 4 h, then Sodium triacetoxyborohydride (0.13 g, 0.63 mmol) was added. After stirring overnight, a mixture of products was observed. The reaction mixture was partitioned between DCM and satd. sodium bicarbonate; the organic was washed with brine and dried over sodium sulfate. Chromatography (0-100% EtOAc:Hex) afforded 9-Ethyl-2-nitro-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocyclohepten-7-ol (23 mg, 31%) and 9-Ethyl-7-morpholin-4-yl-2-nitro-6,7,8,9-tetrahydro-5-oxa-9-aza-benzocycloheptene (60 mg, 60%). 1H-NMR (CDCl3): 7.55 (m, 2H), 6.88 (m, 1H), 4.45 (m, 1H), 4.34 (m, 1H), 3.72 (m, 5H), 3.37 (m, 3H), 3.01 (m, 1H), 2.66 (m, 4H), 1.25 (t, 3H, J=7.0 Hz).

Workup

  1. additiona mixture of products
  2. customThe reaction mixture was partitioned between DCM
  3. washthe organic was washed with brine
  4. dry with materialdried over sodium sulfate

Sources & evidence

ORD record
ord-508789ec1d8e4cd0aa5193d011dcfe43
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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