Tetrahydrofuran → HCID 71227791, compound

HRID 1483840Notes

Reaction equation

HRID 1483840 reaction equation
[CH2:1]([N:8]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C@H:9]1[CH2:13][CH2:12][C@H:11](C(OCC2C=CC=CC=2)=O)[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:31][Mg+].[Br-].[NH4+].[Cl-].[CH2:36]1[CH2:40][O:39]CC1>>[CH2:24]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C@H:9]1[CH2:13][CH2:12][C@H:11]([C:40]([OH:39])([CH3:36])[CH3:31])[CH2:10]1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 131736724HCID 131736724, compoundHCID 178418689HCID 178418689, compound

Product 1

HCID 71227791HCID 71227791, compoundYield 133%

Procedure

To a 0° C. solution of trans-benzyl 3-(dibenzylamino)cyclopentanecarboxylate (2.8 g, 7 mmol) in THF (250 mL) was added dropwise MeMgBr (23 mL, 70 mmol). After the addition, the reaction mixture was stirred at room temperature overnight. TLC (PE) showed the reaction was complete. The mixture was cooled and poured into sat. NH4Cl (300 mL) and extracted with EtOAc (100 mL*3). The combined extracts were dried over Na2SO4, filtered and concentrated in vacuo to give crude 2-(trans-3-(dibenzylamino)cyclopentyl)propan-2-ol (3 g, 133%) as a yellow liquid.

Workup

  1. additionAfter the addition
  2. temperatureThe mixture was cooled
  3. extractionextracted with EtOAc (100 mL*3)
  4. dry with materialThe combined extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-01da7dc4b2cf433391ab11e2785219e1
Source dataset
uspto-grants-2016_08
Patent number
US09416132B2

Reaction notes

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