Water → HCID 68650252, compound

HRID 402253Notes

Reaction equation

HRID 402253 reaction equation
[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[NH:25][CH2:24][CH2:23][CH2:22][C:21]([C:26]([NH:28][C:29]4[CH:34]=[CH:33][C:32]([S:35]([CH2:37][C:38]5[N:42]([CH2:43][CH2:44][CH3:45])[CH:41]=[N:40][CH:39]=5)=[O:36])=[CH:31][CH:30]=4)=[O:27])=[CH:20][C:19]=3[CH:46]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4].[CH:47]1([CH:50]=O)[CH2:49][CH2:48]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].O>ClCCCl>[CH2:1]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[CH:16]=[CH:17][C:18]3[N:25]([CH2:50][CH:47]4[CH2:49][CH2:48]4)[CH2:24][CH2:23][CH2:22][C:21]([C:26]([NH:28][C:29]4[CH:30]=[CH:31][C:32]([S:35]([CH2:37][C:38]5[N:42]([CH2:43][CH2:44][CH3:45])[CH:41]=[N:40][CH:39]=5)=[O:36])=[CH:33][CH:34]=4)=[O:27])=[CH:20][C:19]=3[CH:46]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 123114CyclopropanecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 68649961HCID 68649961, compound

Product 1

HCID 68650252HCID 68650252, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of (−)-8-(4-(2-butoxyethoxy)phenyl)-N-(4-(((1-propylimidazol-5-yl)methyl)sulfinyl)phenyl)-1,2,3,4-tetrahydro-1-benzazocine-5-carboxamide (120 mg) in 1,2-dichloroethane (10 ml), cyclopropanecarboxaldehyde (65.6 mg) and sodium triacetoxyborohydride (119 mg) were added. The mixture was stirred at room temperature for overnight. The reaction mixture was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated NaHCO3, brine, and dried over MgSO4. The volatile materials were removed in vacuo and the residue was purified by column chromatography (basic silicagel, ethyl acetate) to give (−)-8-(4-(2-butoxyethoxy)phenyl)-1-(cyclopropylmethyl)-N-(4-(((1-propylimidazol-5-yl)methyl)sulfinyl)phenyl)-1,2,3,4-tetrahydro-1-benzazocine-5-carboxamide (55 mg)(compound 57) as a yellow amorphous.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated NaHCO3, brine
  3. dry with materialdried over MgSO4
  4. customThe volatile materials were removed in vacuo
  5. customthe residue was purified by column chromatography (basic silicagel, ethyl acetate)

Sources & evidence

ORD record
ord-071bf978ac3a4c77b6cbbf63c4923d70
Source dataset
uspto-grants-2014_06
Patent number
US08741943B2

Reaction notes

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