Sodium cyanoborohydride → HCID 19029368, compound

HRID 2256319Notes

Reaction equation

HRID 2256319 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:23][CH:24]=O)[CH2:10][C:11]([N:13]2[CH2:22][CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14]2)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8].Cl.[C:27]1([C:33]2([OH:39])[CH2:38][CH2:37][NH:36][CH2:35][CH2:34]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[BH3-]C#N.[Na+]>CO.C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]([CH2:23][CH2:24][N:36]2[CH2:37][CH2:38][C:33]([OH:39])([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH2:34][CH2:35]2)[CH2:10][C:11]([N:13]2[CH2:22][CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14]2)=[O:12])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 186143834-Phenylpiperidin-4-ol hydrochlorideHCID 19029354HCID 19029354, compound

Product 1

HCID 19029368HCID 19029368, compoundYield 70.9%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

2-[3-(3,4-dichlorophenyl)-1,5-dioxopentyl]-1,2,3,4-tetrahydroisoquinoline (800 mg), in MeOH/THF (1:1, 20 mL) was treated sequentially with molecular sieves 3A (900 mg), 4-phenyl-4-hydroxypiperidine HCl (900 mg) and NaBH3CN (130 mg). The resulting mixture was stirred at room temperature for 18 hours. The reaction mixture was with quenched with water (20 mL) and diluted with CH2Cl2 (50 mL). The organic layer was separated and the aqueous layer extracted with CH2Cl2 (3×50 mL) The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure to give the crude oil. Silica gel chromatography eluting with 1-2% MeOH/CH2Cl2 gave the title compound (810 mg). Mass spectrum (FAB): 537.2075.

Workup

  1. customwith quenched with water (20 mL)
  2. additiondiluted with CH2Cl2 (50 mL)
  3. customThe organic layer was separated
  4. extractionthe aqueous layer extracted with CH2Cl2 (3×50 mL) The combined organic layers
  5. dry with materialwere dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customto give the crude oil
  9. washSilica gel chromatography eluting with 1-2% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-e3a594622c8f4f96aa5bc85caf03a9b8
Source dataset
uspto-grants-1997_08
Patent number
US05654316

Reaction notes

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