Sodium cyanoborohydride → HCID 19027117, compound

HRID 1032980Notes

Reaction equation

HRID 1032980 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 8, 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 (3x 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 (3x 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-74442b00f52e48218a735825abe32d9f
Source dataset
uspto-grants-1994_05
Patent number
US05308850

Reaction notes

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