Formaldehyde → HCID 86705517, compound

HRID 2279518Notes

Reaction equation

HRID 2279518 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@H:9]([N:22]2[C:30](=[O:31])[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:23]2=[O:32])[C@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[C:15](OC(C)(C)C)=O)[CH:5]=[CH:6][C:7]=1[Cl:8].C=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:9]([C@H:10]2[CH2:14][CH2:13][CH2:12][N:11]2[CH3:15])[N:22]2[C:23](=[O:32])[C:24]3[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:30]2=[O:31])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 86705515HCID 86705515, compound

Product 1

HCID 86705517HCID 86705517, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 242 (0.400 g, 0.972 mmol) and DCE (10 mL) at RT was added TEA (0.295 g, 2.91 mmol) and formaldehyde (0.631 g, 7.77 mmol) and the reaction was stirred for 10 min before NaBH(OAc)3 (0.824 g, 3.89 mmol) was added. The reaction was stirred for 2 h at RT. The reaction was poured into satd. aq. Na2CO3 and extracted with DCM. The combined organic extracts were dried (MgSO4), filtered, and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with a hexane/EtOAc gradient (3:1 to 1:1) to afford 0.3 g (79.3%) of 2-((S)-(3,4-dichlorophenyl)((R)-1-methylpyrrolidin-2-yl)methyl)isoindoline-1,3-dione (244).

Workup

  1. additionwas added
  2. additionThe reaction was poured into satd
  3. extractionaq. Na2CO3 and extracted with DCM
  4. dry with materialThe combined organic extracts were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by SiO2 chromatography
  8. washeluting with a hexane/EtOAc gradient (3:1 to 1:1)

Sources & evidence

ORD record
ord-bee25bb4d9ef4272993659b84f694b44
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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