Sodium cyanoborohydride → HCID 19027117, compound

HRID 1492409Notes

Reaction equation

HRID 1492409 reaction equation
[Cl:1][C:2]1[CH:43]=[CH:42][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH2:17][C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)=[CH:13][CH:14]=3)[C:9]([C:28](=O)[C:29]([CH3:32])([CH3:31])[CH3:30])=[C:8]2[CH2:34][C:35]([CH3:41])([CH3:40])[C:36]([O:38][CH3:39])=[O:37])=[CH:4][CH:3]=1.[BH3-]C#N.[Na+]>ClC(Cl)C.[Zn+2].[I-].[I-]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH2:17][C:18]4[CH:27]=[CH:26][C:25]5[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=5)[N:19]=4)=[CH:13][CH:14]=3)[C:9]([CH2:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[C:8]2[CH2:34][C:35]([CH3:41])([CH3:40])[C:36]([O:38][CH3:39])=[O:37])=[CH:42][CH:43]=1

Participants

5

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 18947574HCID 18947574, compound

Product 1

HCID 19027117HCID 19027117, compound

Reagents, catalysts & solvents 2

HCID 9883512zinc(II)iodideCatalystHCID 63651,1-DichloroethaneSolvent

Procedure

A mixture of methyl 3-[1-(4-chlorobenzyl)-3-trimethylacetyl-5-(quinolin-2-ylmethoxy) indol-2-yl]-2,2-dimethylpropanoate (EP 419,049; Example 54, Step A) (15.64 g), ZnI2 (25.2 g), and NaBH3CN (16.4 g) in 210 mL dichloroethane was stirred using a mechanical stirrer at r.t. for 30 minutes and then at 73° C. for 3 hours. The reaction mixture was allowed to cool, poured onto NH4OAc (aq), and extracted (3×EtOAc). The organic phase was dried (MgSO4), evaporated, and the residue chromatographed (silica gel; ether/hexane 1:3) to give the title compound as a solid.

Workup

  1. customat r.t.
  2. customfor 30 minutes
  3. temperatureto cool
  4. additionpoured onto NH4OAc (aq)
  5. extractionextracted (3×EtOAc)
  6. dry with materialThe organic phase was dried (MgSO4)
  7. customevaporated
  8. customthe residue chromatographed (silica gel; ether/hexane 1:3)

Sources & evidence

ORD record
ord-b6a960153e0641cba57f4ed42a551cd7
Source dataset
uspto-grants-1994_12
Patent number
US05374635

Reaction notes

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