Sodium triacetoxyborohydride → HCID 57204187, compound

HRID 2298065Notes

Reaction equation

HRID 2298065 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([CH:22]=O)=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5].[NH2:24][CH:25]1[CH2:30][CH2:29][CH:28]([CH2:31][NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36])[CH2:27][CH2:26]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[Cl:1][C:2]1[CH:21]=[CH:20][C:19]([CH2:22][NH:24][CH:25]2[CH2:30][CH2:29][CH:28]([CH2:31][NH:32][C:33](=[O:39])[O:34][C:35]([CH3:36])([CH3:38])[CH3:37])[CH2:27][CH2:26]2)=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:5]

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 120853462-Chloro-5-formyl-N-(tricyclo [3.3.1.13,7]dec-1-ylmethyl)-benzamideHCID 218825401,1-Dimethylethyl N-((4-aminocyclohexyl)methyl)carbamate

Product 1

HCID 57204187HCID 57204187, compoundYield 52.8%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

Prepared according to the method described in Example 31b from 2-chloro-5-formyl-N-(tricyclo [3.3.1.13,7]dec-1-ylmethyl)-benzamide (0.30 g, Example 31a), [(4-aminocyclohexyl)methyl]-carbamic acid, 1,1-dimethylethyl ester (0.207 g, WO 97/32882), sodium triacetoxyborohydride (0.135 g) and 1,2-dichloroethane (10 ml). The residue was purified by chromatography over silica gel eluting with ethyl acetate: iso-hexane (1:1) then ethyl acetate: ethanol (9:1) to give the subtitle compound as a colourless oil (0.26 g).

Workup

  1. customPrepared
  2. customThe residue was purified by chromatography over silica gel eluting with ethyl acetate: iso-hexane (1:1)

Sources & evidence

ORD record
ord-92a1936245834318919221e5fccb12c2
Source dataset
uspto-grants-2002_12
Patent number
US06492355B1

Reaction notes

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