Morpholine → HCID 57949327, compound

HRID 2427547Notes

Reaction equation

HRID 2427547 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[CH3:7][C:8]1[CH:9]=[C:10]([CH:30]=O)[CH:11]=[C:12]2[C:16]=1[C:15](=[O:17])[N:14]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=1)[CH2:13]2.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH3:7][C:8]1[CH:9]=[C:10]([CH2:30][N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)[CH:11]=[C:12]2[C:16]=1[C:15](=[O:17])[N:14]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]([O:25][C:26]([F:29])([F:27])[F:28])=[CH:23][CH:24]=1)[CH2:13]2

Participants

5

Reactant 3

HCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 57949729HCID 57949729, compound

Product 1

HCID 57949327HCID 57949327, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Morpholine (8.2 mg, 0.094 mmol) was dissolved in dichloromethane (2.0 mL) and 7-Methyl-1-oxo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-1H-isoindole-5-carbaldehyde (30.0 mg, 0.085 mmol) was added. The mixture was stirred for ten minutes and sodium triacetoxy borohydride (29.7 mg, 0.14 mmol) was added and the reaction was allowed to stir overnight. The reaction was then diluted with dichloromethane, washed with saturated sodium bicarbonate and brine, dried over sodium sulfate, filtered and concentrated. Column chromatography (20% MeOH/EtOAc) provided the title compound as a colourless oil (13.3 mg, 37%). 1H NMR (300 MHz, CDCl3): δ 7.35 (d, 2H), 7.19 (d, 4H), 4.78 (s, 2H), 4.23 (s, 2H), 3.72 (t, 4H), 3.53 (s, 2H), 2.76 (s, 3H), 2.45 (t, 4H).

Workup

  1. stirringto stir overnight
  2. washwashed with saturated sodium bicarbonate and brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ec8fdbfcb3a44b918c576d922e4e21c3
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

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