Dichloromethane → HCID 23138794, compound

HRID 1171733Notes

Reaction equation

HRID 1171733 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][CH2:7][CH2:8][N:9]1[N:13]=[N:12][C:11](/[CH:14]=[C:15]2\[CH2:16][N:17]([C:22]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:18][CH2:19][C:20]\2=[O:21])=[N:10]1)=[O:5])[CH3:2].[BH4-].[Na+].ClCCl>C(O)C>[CH2:1]([O:3][C:4]([CH2:6][CH2:7][CH2:8][N:9]1[N:13]=[N:12][C:11](/[CH:14]=[C:15]2\[CH2:16][N:17]([C:22]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:18][CH2:19][CH:20]\2[OH:21])=[N:10]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 23138831HCID 23138831, compound

Product 1

HCID 23138794HCID 23138794, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(E)-3-({2-[3-(Ethoxycarbonyl)propyl]-2H-tetrazol-5-yl}methylidene)-1-(triphenylmethyl)piperidin-4-one (3.93 g) was reduced with sodium borohydride (281 mg) in a mixed solvent of dichloromethane (30 ml) and ethanol (30 ml) in a similar manner to that mentioned in Example 138 (c), and the crude product obtained by conventional extraction procedures was purified by chromatography on silica gel using a mixture of ethyl acetate and hexane (1:9 to 7:3) as the eluent to afford the title compound as a yellow oil (1.46 g, yield: 37%).

Workup

  1. customthe crude product obtained by conventional extraction procedures
  2. customwas purified by chromatography on silica gel using
  3. additiona mixture of ethyl acetate and hexane (1:9 to 7:3) as the eluent

Sources & evidence

ORD record
ord-5c59255ba917438a828f7e09d6cae192
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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