Glycine, N-methyl-, ethyl ester → HCID 178472701, compound

HRID 713871Notes

Reaction equation

HRID 713871 reaction equation
[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[C:17](C=O)[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[CH3:24][NH:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28].[BH3-][C:33]#N.[Na+]>C(O)C>[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([O:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[CH:18]=[C:17]([CH2:24][N:25]([CH3:33])[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 95849Glycine, N-methyl-, ethyl esterHCID 5003444Sodium cyanoborohydrideHCID 178445787HCID 178445787, compound

Product 1

HCID 178472701HCID 178472701, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
23 °C

Procedure

A mixture of 6-(trans-4-tert-butylcyclohexyloxy)-2-naphthaldehyde (155 mg, 0.5 mmol) and ethyl 2-(methylamino)acetate (117 mg, 1.0 mmol, 2.0 equiv) in anhydrous ethanol (20 mL) was refluxed for 2 hr and evaporated in vacuum to dryness. Anhydrous EtOH was added and refluxed for 1 hr, and then the mixture was cooled to 23° C. NaBH3CN (60 mg, 1.0 mmol, 2.0 equiv) was added. The resulted mixture was refluxed for 1 h. The reaction mixture was concentrated in vacuum and the residue was purified by chromatography with silica gel (dichloromethane:methanol 20:1) to give product ethyl 2-(((6-(trans-4-tert-butylcyclohexyloxy)naphthalen-2-yl)methyl)(methyl)amino)acetate as a white solid (82 mg, yield: 40%). ESI-MS: 411.3 (M+H)+. HPLC: 98.93%. 1H NMR (400 MHz, CDCl3) δ 7.71-7.67 (m, 3H), 7.00 (d, 1H), 7.14-7.13 (m, 2H), 4.30-4.28 (m, 1H), 4.18 (q, 2H), 3.82 (s, 3H), 3.30 (s, 2H), 2.45 (s, 3H), 2.29-2.27 (m, 2H), 1.91-1.88 (m, 2H), 1.46-1.42 (M, 2H), 1.29-1.22 (m, 3H), 0.90 (s, 9H).

Workup

  1. temperaturewas refluxed for 2 hr
  2. customevaporated in vacuum to dryness
  3. additionAnhydrous EtOH was added
  4. temperaturerefluxed for 1 hr
  5. temperatureThe resulted mixture was refluxed for 1 h
  6. concentrationThe reaction mixture was concentrated in vacuum
  7. customthe residue was purified by chromatography with silica gel (dichloromethane:methanol 20:1)

Sources & evidence

ORD record
ord-3222acbba2aa4632b0d2e0ae6c7c1590
Source dataset
uspto-grants-2015_11
Patent number
US09186367B2

Reaction notes

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