Ammonium Hydroxide → HCID 86753730, compound

HRID 362783Notes

Reaction equation

HRID 362783 reaction equation
[NH2:1][C:2]1[C:7]2[CH2:8][CH2:9][O:10][C:6]=2[C:5]([C:11]([O:13][C@H:14]2[CH2:19][CH2:18][N:17](C(OC(C)(C)C)=O)[CH2:16][C@H:15]2[O:27][CH3:28])=[O:12])=[CH:4][C:3]=1[Cl:29].[NH4+].[OH-]>O1CCCC1.Cl>[NH2:1][C:2]1[C:7]2[CH2:8][CH2:9][O:10][C:6]=2[C:5]([C:11]([O:13][C@H:14]2[CH2:19][CH2:18][NH:17][CH2:16][C@H:15]2[O:27][CH3:28])=[O:12])=[CH:4][C:3]=1[Cl:29]

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 86753731HCID 86753731, compound

Product 1

HCID 86753730HCID 86753730, compoundYield 26.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of intermediate (5) (32 g) in tetrahydrofuran (500 ml) and hydrochloric acid (50 ml) was stirred and refluxed for 30 minutes. The reaction mixture was cooled and alkalized with NH4OH. The layers were separated. The aqueous layer was extracted with tetrahydrofuran. The separated organic layer was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /(CH3OH/NH3) 93/7). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from acetonitrile. The precipitate was filtered off and dried (vacuum; 80° C.), yielding 6.4 g of (±)-cis-3-methoxy-4-piperidinyl 4-amino-5-chloro-2,3-dihydro-7-benzofurancarboxylate (26%) (intermediate 6).

Workup

  1. temperaturerefluxed for 30 minutes
  2. temperatureThe reaction mixture was cooled
  3. customThe layers were separated
  4. extractionThe aqueous layer was extracted with tetrahydrofuran
  5. customThe separated organic layer was evaporated
  6. customThe residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /(CH3OH/NH3) 93/7)
  7. customThe pure fractions were collected
  8. customthe solvent was evaporated
  9. customThe residue was crystallized from acetonitrile
  10. filtrationThe precipitate was filtered off
  11. customdried (vacuum; 80° C.)

Sources & evidence

ORD record
ord-9d9014d843e14c9aa44fd123c1a9fce2
Source dataset
uspto-grants-1999_02
Patent number
US05872131

Reaction notes

Loading…