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Methanol → 5-Chloro-alpha-(4-tert-butoxycarbonylaminomethylphenyl)-2-neopentylaminobenzyl alcohol

HRID 275851
Notes
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Reaction equation

HRID 275851 reaction equation
CO.[NH2:3][C:4]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:5]=1[CH:6]([OH:22])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:9][CH:8]=1.[CH3:28][C:29]([CH3:33])([CH3:32])[CH:30]=O.C([BH3-])#N.[Na+]>C(OC(=O)C)C.C(O)(=O)C>[Cl:27][C:24]1[CH:25]=[CH:26][C:4]([NH:3][CH2:28][C:29]([CH3:33])([CH3:32])[CH3:30])=[C:5]([CH:23]=1)[CH:6]([OH:22])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])=[CH:9][CH:8]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 887MethanolHCID 12417PivalaldehydeHCID 5003444Sodium cyanoborohydrideHCID 545021332-Amino-5-chloro-alpha-(4-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol

Product 1

HCID 543280705-Chloro-alpha-(4-tert-butoxycarbonylaminomethylphenyl)-2-neopentylaminobenzyl alcoholYield 100%

Reagents, catalysts & solvents

2
HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a methanol (8 ml) solution of 2-amino-5-chloro-α-(4-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol (0.83 g) were added trimethyl acetaldehyde (220 mg) and acetic acid (170 mg). The mixture was stirred for 10 minutes at room temperature, to which was added sodium cyano borohydride (160 mg). The mixture was stirred overnight at room temperature, to which was added acetic acid ethyl ester (100 ml). The mixture was washed with water and dried over anhydrous Na2SO4. The solvent was then distilled off, and the residue was purified by means of a silica gel column chromatography to give the object 5-chloro-α-(4-tert-butoxycarbonylaminomethylphenyl)-2-neopentylaminobenzyl alcohol (0.99 g) as a colorless oily product.

Workup

  1. stirringThe mixture was stirred overnight at room temperature, to which
  2. washThe mixture was washed with water
  3. dry with materialdried over anhydrous Na2SO4
  4. distillationThe solvent was then distilled off
  5. customthe residue was purified by means of a silica gel column chromatography

Sources & evidence

ORD record
ord-2efdd3ed1c3c4a8c9ffa11aebead2ebf
Source dataset
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06352982B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes