Sodium borohydride → HCID 23403780, compound

HRID 1064385Notes

Reaction equation

HRID 1064385 reaction equation
[C:1]1([CH:7]2[CH2:12][CH2:11][N:10]([CH2:13][CH:14]3[CH2:20][CH2:19][C:18]4[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=4[C:16](=[O:25])[CH2:15]3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[BH4-].[Na+].CCOCC.[ClH:33]>CO.C(Cl)Cl.CCOCC>[ClH:33].[C:1]1([CH:7]2[CH2:8][CH2:9][N:10]([CH2:13][C@H:14]3[CH2:20][CH2:19][C:18]4[CH:21]=[CH:22][CH:23]=[CH:24][C:17]=4[C@H:16]([OH:25])[CH2:15]3)[CH2:11][CH2:12]2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 4311764Sodium borohydrideHCID 10953452Ether hydrochlorideHCID 22273798HCID 22273798, compound

Product 1

HCID 23403780HCID 23403780, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 21881112Ethyl ether methylene chlorideSolvent

Procedure

0.7 g (2.1 mmol) of (±)-7-[(4-phenylpiperidin-1-yl)methyl]-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one were dissolved in 40 mL of MeOH and 0.35 g of NaBH4 were added portionwise. The reaction mixture was stirred 2 h at room temperature, the MeOH removed in vacuo, then the residue was taken up in 1N NaOH and extracted with CH2Cl2. The organic phase was dried and the solvent was removed in vacuo. The crude product was purified by chromatography, eluting with CH2Cl2 and then with a mixture CH2Cl2/MeOH 100:3 respectively, yielding 100 mg of trans isomer which was dissolved in a mixture CH2Cl2/Et2O: The solution was brought to acidic pH with Et2O/HCl and the solvent was removed in vacuo. The resulting solid was triturated with hot acetone, filtered and dried, yielding 90 mg of the title compound. m.p.>250° C.

Workup

  1. customthe MeOH removed in vacuo
  2. extractionextracted with CH2Cl2
  3. customThe organic phase was dried
  4. customthe solvent was removed in vacuo
  5. customThe crude product was purified by chromatography
  6. washeluting with CH2Cl2
  7. customwith a mixture CH2Cl2/MeOH 100:3 respectively, yielding 100 mg of trans isomer which
  8. customthe solvent was removed in vacuo
  9. customThe resulting solid was triturated with hot acetone
  10. filtrationfiltered
  11. customdried

Sources & evidence

ORD record
ord-ee4e62ed18f648ee8c1987fa0bbba336
Source dataset
uspto-grants-2005_11
Patent number
US06969724B2

Reaction notes

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