HCID 10891827, compound → HCID 86711989, compound

HRID 1051345Notes

Reaction equation

HRID 1051345 reaction equation
[CH2:1]([N:8]([CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C@@H:9]([CH3:15])[C:10]([O:12]CC)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:23][CH2:24][Mg+].[Br-]>C1COCC1.CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4]>[CH2:16]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C@H:9]([C:10]1([OH:12])[CH2:24][CH2:23]1)[CH3:15])[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 10891827HCID 10891827, compoundHCID 178461630HCID 178461630, compound

Product 1

HCID 86711989HCID 86711989, compoundYield 90.3%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 26 (8.80 g, 29.5 mmol) and titanium tetraisopropoxide (1.28 g, 5.90 mmol) in dry THF (100 mL) was added EtMgBr (30 mL, 90 mmol, 3.0 N in THF) at 0° C. After stirring at RT overnight, the mixture was cooled to 0° C. and quenched with NH4Cl solution. The solid was filtered off and filtrate was extracted with EtOAc. The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by SiO2 chromatography eluting with petroleum ether/EtOAc (20:1) to afford 7.5 g (90%) of 7.5 g (90%) of (S)-1-(1-(dibenzylamino)ethyl)cyclopropanol (28). LCMS (ESI) m/z: 282.1 [M+H]+.

Workup

  1. temperaturethe mixture was cooled to 0° C.
  2. customquenched with NH4Cl solution
  3. filtrationThe solid was filtered off
  4. extractionfiltrate was extracted with EtOAc
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by SiO2 chromatography
  9. washeluting with petroleum ether/EtOAc (20:1)

Sources & evidence

ORD record
ord-3ef72b1edc84457998f22a6651cc09d2
Source dataset
uspto-grants-2016_07
Patent number
US09388171B2

Reaction notes

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