HCID 57983094, compound → HCID 57983142, compound

HRID 1869241Notes

Reaction equation

HRID 1869241 reaction equation
[C:1]1([CH2:7][N:8]([CH2:16][C@@H:17]2[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19][C@H:18]2[OH:30])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CC(O)C>[C:1]1([CH2:7][N:8]([CH2:16][C@@H:17]2[CH2:22][CH2:21][NH:20][CH2:19][C@H:18]2[OH:30])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 1

HCID 57983094HCID 57983094, compound

Product 1

HCID 57983142HCID 57983142, compoundYield 100.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

A mixture of intermediate (70) (0.284 mol) in 2-propanol (1000 ml) and a mixture of 6N HCL in 2-propanol (250 ml) was stirred and refluxed for 15 minutes and then cooled. The solvent was evaporated. A 5% aqueous NaOH solution (750 ml) was added. The mixture was extracted three times with DCM. The organic layer was separated, dried, filtered and the solvent was evaporated, yielding 88.95 g of (trans)-4-[[bis(phenylmethyl)amino]methyl]-3-piperidinol (intermediate 71).

Workup

  1. temperaturerefluxed for 15 minutes
  2. temperaturecooled
  3. customThe solvent was evaporated
  4. additionA 5% aqueous NaOH solution (750 ml) was added
  5. extractionThe mixture was extracted three times with DCM
  6. customThe organic layer was separated
  7. customdried
  8. filtrationfiltered
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-8920dcaf18c442f797cf2c779456eacd
Source dataset
uspto-grants-2009_12
Patent number
US07638535B2

Reaction notes

Loading…