Diisopropylethylamine → {[6-(4-Tert-butyl-cyclohexyloxy)-8-methyl-naphthalen-2-ylmethyl]-amino}-acetic acid methyl ester

HRID 2404200Notes

Reaction equation

HRID 2404200 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[C:20]([CH3:22])[CH:21]=2)[CH:18]=[C:17]([CH:23]=O)[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:26][O:27][C:28](=[O:31])[CH2:29][NH2:30].C(N(CC)C(C)C)(C)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.C(Cl)Cl>[CH3:26][O:27][C:28](=[O:31])[CH2:29][NH:30][CH2:23][C:17]1[CH:16]=[CH:15][C:14]2[C:19](=[C:20]([CH3:22])[CH:21]=[C:12]([O:11][CH:8]3[CH2:7][CH2:6][CH:5]([C:1]([CH3:3])([CH3:4])[CH3:2])[CH2:10][CH2:9]3)[CH:13]=2)[CH:18]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 122755Glycine methyl ester hydrochlorideHCID 5049666Sodium triacetoxyborohydrideHCID 866684296-(4-Tert-butyl-cyclohexyloxy)-8-methyl-naphthalene-2-carbaldehyde

Product 1

HCID 66926551{[6-(4-Tert-butyl-cyclohexyloxy)-8-methyl-naphthalen-2-ylmethyl]-amino}-acetic acid methyl esterYield 88.9%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 6-(4-tert-butyl-cyclohexyloxy)-8-methyl-naphthalene-2-carbaldehyde (50 mg, 0.15 mmol), glycine methyl ester, hydrochloride (27 mg, 0.22 mmol) and N,N-diisopropylethylamine (DIEA) (34 uL) in 1,2-dichloroethane (2 mL) was stirred for 1 hour at room temperature. Then sodium triacetoxyborohydride (52 mg, 0.25 mmol) was added and stirred for 3 hrs. The reaction was diluted with methylene chloride and washed with saturated sodium bicarbonate aqueous, dried over MgSO4, filtered, and concentrated. The crude was purified via silica gel column chromatography eluted 0-5% MeOH in methylene chloride to give the light brown solid (53 mg, yield: 86%). ESI-MS: 420.30 (M+23)+.

Workup

  1. washwashed with saturated sodium bicarbonate aqueous
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude was purified via silica gel column chromatography
  6. washeluted 0-5% MeOH in methylene chloride

Sources & evidence

ORD record
ord-1bcd70ff18454a80990d0f23c39fcf29
Source dataset
uspto-grants-2014_08
Patent number
US08802659B2

Reaction notes

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