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Glyceraldehyde → Ethyl acetate methanol ammonium hydroxide

HRID 377415
Notes
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Reaction equation

HRID 377415 reaction equation
[N:1]1(CC[O:8]C2C=CC(CC3C4C=CC=CC=4SC=3C3C=CC(CCN)=CC=3)=CC=2)CCCC1.[O:34]=[CH:35][CH:36]([CH2:38][OH:39])O.[C:40](O[BH-](OC(=O)C)OC(=O)C)(=[O:42])[CH3:41].[Na+]>ClCCl.CO>[NH4+:1].[OH-:8].[CH3:35][OH:34].[CH3:41][CH2:40][O:42][C:38]([CH3:36])=[O:39]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 751GlyceraldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 224627162-[4-(2-Aminoethyl)phenyl]-3-[4-[2-(1-pyrrolidinyl)ethoxy]benzyl]benzo[b]thiophene

Product 1

HCID 21901312Ethyl acetate methanol ammonium hydroxide

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent
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Procedure

3-[4-[2-(1-Pyrrolidinyl)ethoxy]benzyl]-2-[4-(2-aminoethyl)phenyl]benzo[b]thiophene (113 mg) was dissolved in dichloromethane:methanol (2:1, 6.0 mL), treated with glyceraldehyde (25 mg) and sodium triacetoxyborohydride (60 mg) sequentially and allowed to stir at ambient temperature for 4 h. The reaction mixture was concentrated, and column chromatography with NH4OH:MeOH:EtOAc (3:7:90) afforded the product (56 mg).

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-1a415f14033b4c91b21f175517078ddb
Source dataset
uspto-grants-2000_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06025382

Reaction notes

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