Sodium borohydride → HCID 23138807, compound

HRID 1171742Notes

Reaction equation

HRID 1171742 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[CH:14]=[C:13](/[CH:15]=[C:16]2\[CH2:17][N:18]([C:23]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:19][CH2:20][C:21]\2=[O:22])[N:12]=[N:11]1)=[O:5])[CH3:2].[BH4-].[Na+]>>[CH2:1]([O:3][C:4]([CH2:6][CH2:7][CH2:8][CH2:9][N:10]1[CH:14]=[C:13](/[CH:15]=[C:16]2\[CH2:17][N:18]([C:23]([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH2:19][CH2:20][CH:21]\2[OH:22])[N:12]=[N:11]1)=[O:5])[CH3:2]

Participants

3

Reactant 2

HCID 4311764Sodium borohydrideHCID 23139139HCID 23139139, compound

Product 1

HCID 23138807HCID 23138807, compoundYield 98.2%

Procedure

(E)-3-({1-[4-(Ethoxycarbonyl)butyl]-1H-1,2,3-triazol-4-yl}methylidene)-1-(triphenylmethyl)piperidin-4-one (18.87 g) was allowed to react with sodium borohydride (1.32 g) in a similar manner to that described in Example 132 (d). The crude product obtained by extraction was purified by chromatography on silica gel using a mixture of ethyl acetate and hexane (4:6 to 6:4), followed by a mixture of methanol and dichloromethane (5:9 to 10:90) as eluents to afford the title compound as a pale brown amorphous solid (18.59 g).

Workup

  1. customThe crude product obtained by extraction
  2. customwas purified by chromatography on silica gel using
  3. additiona mixture of ethyl acetate and hexane (4:6 to 6:4)
  4. additionfollowed by a mixture of methanol and dichloromethane (5:9 to 10:90) as eluents

Sources & evidence

ORD record
ord-7519c73c4a194120a452e6f2c0c1e72a
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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