Methanol → 5-Chloro-alpha-(3-tert-butoxycarbonylaminophenyl)-2-neopentylaminobenzyl alcohol

HRID 275848Notes

Reaction equation

HRID 275848 reaction equation
CO.[NH2:3][C:4]1[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][C:5]=1[CH:6]([OH:21])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:8]=1.[CH3:27][C:28]([CH3:32])([CH3:31])[CH:29]=O.C([BH3-])#N.[Na+]>C(OC(=O)C)C.C(O)(=O)C>[Cl:26][C:23]1[CH:24]=[CH:25][C:4]([NH:3][CH2:27][C:28]([CH3:32])([CH3:31])[CH3:29])=[C:5]([CH:22]=1)[CH:6]([OH:21])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:8]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 12417PivalaldehydeHCID 5003444Sodium cyanoborohydrideHCID 54051866HCID 54051866, compound

Product 1

HCID 538324135-Chloro-alpha-(3-tert-butoxycarbonylaminophenyl)-2-neopentylaminobenzyl alcoholYield 89.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a methanol (4 ml) solution of 2-amino-5-chloro-α-(3-tert-butoxycarbonylaminophenyl) benzyl alcohol (0.4 g) were added trimethyl acetaldehyde (109 mg) and acetic acid (76 mg). The mixture was stirred for 10 minutes at room temperature, to which was added sodium cyano borohydride (79 mg). The mixture was stirred for one hour at room temperature, to which was added acetic acid ethyl ester (50 ml). The mixture was washed with water and dried over anhydrous MgSO4. 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-(3-tert-butoxycarbonylaminophenyl)-2-neopentylaminobenzyl alcohol (0.43 g) as a colorless amorphous solid product.

Workup

  1. stirringThe mixture was stirred for one hour at room temperature, to which
  2. washThe mixture was washed with water
  3. dry with materialdried over anhydrous MgSO4
  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-c87609a865e3424f8211c7f6361e52b1
Source dataset
uspto-grants-2002_03
Patent number
US06352982B1

Reaction notes

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