HCID 86585402, compound → HCID 66706457, compound

HRID 1879842Notes

Reaction equation

HRID 1879842 reaction equation
[NH2:1][C:2]1[C:7]2[CH2:8][C:9]([CH3:12])([CH3:11])[O:10][C:6]=2[C:5]([C:13]([NH:15][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])=[O:14])=[CH:4][C:3]=1[Cl:31]>Cl.CC(O)C.CO>[NH2:1][C:2]1[C:7]2[CH2:8][C:9]([CH3:11])([CH3:12])[O:10][C:6]=2[C:5]([C:13]([NH:15][CH2:16][C@@H:17]2[CH2:22][CH2:21][NH:20][CH2:19][C@H:18]2[OH:30])=[O:14])=[CH:4][C:3]=1[Cl:31]

Participants

5

Reactant 1

HCID 86585402HCID 86585402, compound

Product 1

HCID 66706457HCID 66706457, compoundYield 73%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 3776IsopropanolSolvent

Procedure

A mixture of intermediate (26) (0.011 mol) in a mixture of HCl in 2-propanol (12 ml) and methanol (100 ml) was stirred and refluxed for 30 minutes. The mixture was cooled and the solvent was evaporated. The residue was partitioned between water/NH3 and DCM. The organic layer was separated, dried, filtered and the solvent was evaporated, yielding 2.84 g (73%) of (−)-(trans)-4-amino-5-chloro-2,3-dihydro-N-[(3-hydroxy-4-piperidinyl)methyl]-2,2-dimethyl-7-benzofurancarboxamide (interm. 14). A sample (0.5 g) was crystallized from ACN with a drop of water, filtered off and dried, yielding 0.2 g of intermediate (14) [mp. 116° C.; [α]D20=−15.91° (c=25.14 mg/5 ml in CH3OH)].

Workup

  1. temperaturerefluxed for 30 minutes
  2. temperatureThe mixture was cooled
  3. customthe solvent was evaporated
  4. customThe residue was partitioned between water/NH3 and DCM
  5. customThe organic layer was separated
  6. customdried
  7. filtrationfiltered
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-15b444cf692b46a8a4c8548fcb360497
Source dataset
uspto-grants-2012_11
Patent number
US08318742B2

Reaction notes

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