Acetic Acid → HCID 66958221, compound

HRID 1619114Notes

Reaction equation

HRID 1619114 reaction equation
C(O)(=O)C.[Br:5][C:6]1[CH:14]=[C:13]2[C:9]([C:10]3([CH2:20][CH2:19][C:18](=O)[CH2:17][CH2:16]3)[C:11](=[O:15])[NH:12]2)=[CH:8][CH:7]=1.[NH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[Br:5][C:6]1[CH:14]=[C:13]2[C:9]([C:10]3([CH2:20][CH2:19][CH:18]([N:22]4[CH2:27][CH2:26][O:25][CH2:24][CH2:23]4)[CH2:17][CH2:16]3)[C:11](=[O:15])[NH:12]2)=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 66953983HCID 66953983, compound

Product 1

HCID 66958221HCID 66958221, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
0 °C

Procedure

Acetic acid (74 μl, 1.29 mmol) was added to a stirred solution of 6′-bromospiro[cyclohexane-1,3′-indoline]-2′,4-dione (preparation 21a, 0.38 g, 1.29 mmol) and morpholine (123 μl, 1.1 mmol) in 1,2-dichloroethane (5 mL). The mixture was cooled to 0° C. and sodium triacetoxy borohydride (0.356 g, 1.68 mmol) was added portionwise. After the addition, the cooling bath was removed and the mixture was stirred at room temperature for 18 hours. Water and dichloromethane were added to the reaction mixture and the organic layer was washed with water, dried (MgSO4) and the solvent was evaporated to give the crude oily product as a mixture of isomers. Separation of the isomers was achieved by flash chromatography (98:2 dichloromethane/methanol):

Workup

  1. additionAfter the addition
  2. customthe cooling bath was removed
  3. additionWater and dichloromethane were added to the reaction mixture
  4. washthe organic layer was washed with water
  5. dry with materialdried (MgSO4)
  6. customthe solvent was evaporated
  7. customto give the crude oily product
  8. additionas a mixture of isomers
  9. customSeparation of the isomers

Sources & evidence

ORD record
ord-d3b8a535dee94f56ab06bf27a49d7505
Source dataset
uspto-grants-2014_07
Patent number
US08772288B2

Reaction notes

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