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

HRID 275845Notes

Reaction equation

HRID 275845 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][CH:10]=[CH:9][C:8]=1[CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].[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][CH:10]=[CH:9][C:8]=1[CH2:13][NH:14][C:15]([O:17][C:18]([CH3:19])([CH3:20])[CH3:21])=[O:16]

Participants

7

Reactant 4

HCID 887MethanolHCID 12417PivalaldehydeHCID 5003444Sodium cyanoborohydrideHCID 539893822-Amino-5-chloro-alpha-(2-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol

Product 1

HCID 542161415-Chloro-alpha-(2-tert-butoxycarbonylaminomethylphenyl)-2-neopentylaminobenzyl alcoholYield 102.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a methanol (5 ml) solution of 2-amino-5-chloro-α-(2-tert-butoxycarbonylaminomethylphenyl)benzyl alcohol (0.5 g) were added trimethyl acetaldehyde (132 mg) and acetic acid (92 mg). The mixture was stirred for 10 minutes at room temperature, to which was added sodium cyano borohydride (97 mg), followed by stirring for one hour at room temperature. To the reaction mixture was added acetic acid ethyl ester (50 ml). The mixture was washed with water and dried over anhydrous Na2SO4. The solvent was then distilled off. The residue was purified by means of a silica gel column chromatography to give the object 5-chloro-α-(2-tert-butoxycarbonylaminomethylphenyl)-2-neopentylaminobenzyl alcohol (0.61 g) as a colorless oily product.

Workup

  1. stirringby stirring for one hour at room temperature
  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-fd5d7ef9b4264046b14cd5f208a34ba8
Source dataset
uspto-grants-2002_03
Patent number
US06352982B1

Reaction notes

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