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Sodium triacetoxyborohydride → (S)-2-Chloro-5-[3-[(2-hydroxyproply)amino]propyl]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide, hydrochloride salt

HRID 1816054
Notes
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Reaction equation

HRID 1816054 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[Cl:15][C:16]1[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][CH:38]=O)=[CH:32][C:17]=1[C:18]([NH:20][CH2:21][C:22]12[CH2:31][CH:26]3[CH2:27][CH:28]([CH2:30][CH:24]([CH2:25]3)[CH2:23]1)[CH2:29]2)=[O:19].[OH:40][C@@H:41]([CH3:44])[CH2:42][NH2:43]>ClCCl>[ClH:15].[Cl:15][C:16]1[CH:35]=[CH:34][C:33]([CH2:36][CH2:37][CH2:38][NH:43][CH2:42][C@@H:41]([OH:40])[CH3:44])=[CH:32][C:17]=1[C:18]([NH:20][CH2:21][C:22]12[CH2:31][CH:26]3[CH2:27][CH:28]([CH2:30][CH:24]([CH2:25]3)[CH2:23]1)[CH2:29]2)=[O:19]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 5049666Sodium triacetoxyborohydrideHCID 7311736(S)-(+)-1-Aminopropan-2-olHCID 120853482-Chloro-5(3-oxopropyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

Product 1

HCID 10139105(S)-2-Chloro-5-[3-[(2-hydroxyproply)amino]propyl]-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide, hydrochloride saltYield 60.1%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

Sodium triacetoxyborohydride (0.6 g) was added to a solution of 2-chloro-5-(3-oxopropyl)-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide (0.5 g, Example 14b) and (S)-2-hydroxypropylamine (0.31 g) in dichloromethane (5 ml). After 24 h the crude reaction mixture was purified by flash chromatography (eluting with 5-20% methanol in dichloromethane +1% ammonia) and the hydrochloride salt precipitated from ether/methanol 19: 1, to afford the title compound as a white solid (0.19 g).

Workup

  1. customAfter 24 h the crude reaction mixture
  2. customwas purified by flash chromatography (eluting with 5-20% methanol in dichloromethane +1% ammonia)
  3. customthe hydrochloride salt precipitated from ether/methanol 19: 1

Sources & evidence

ORD record
ord-5d8fa9e78c51445ba80d8cc5cc1e8544
Source dataset
uspto-grants-2005_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06881754B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes