Triethylamine → HCID 59262167, compound

HRID 534771Notes

Reaction equation

HRID 534771 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C@@H:11]([CH3:22])[CH2:10]2)=[CH:4][CH:3]=1.[CH3:23][O:24][CH2:25][CH:26]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(N(CC)CC)C.C([O-])(O)=O.[Na+]>ClCCCl.C(Cl)Cl.O>[CH3:22][C@H:11]1[CH2:10][N:9]([CH2:8][C:5]2[CH:6]=[CH:7][C:2]([NH:1][CH2:26][CH2:25][O:24][CH3:23])=[CH:3][CH:4]=2)[CH2:14][CH2:13][N:12]1[C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 91563MethoxyacetaldehydeHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 592622171,1-Dimethylethyl (2S)-4-[(4-aminophenyl)methyl]-2-methyl-1-piperazinecarboxylate

Product 1

HCID 59262167HCID 59262167, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1,1-dimethylethyl (2S)-4-[(4-aminophenyl)methyl]-2-methyl-1-piperazinecarboxylate (D2) (0.30 g, 1 mmol), (methyloxy)acetaldehyde (D89), sodium tri(acetoxy)borohydride (0.417 g, 2 mmol) and triethylamine (0.165 mL, 1.2 mmol) in 1,2-DCE (15 mL) was stirred under Ar at room temperature for 19 hours. Saturated NaHCO3 (20 mL) was added and reaction mixture stirred for a further 1 hour. The reaction mixture was further diluted with DCM (25 mL) and water (10 mL). The aqueous layer was then extracted with DCM (×3) and the combined organic layers were dried (Na2SO4) and concentrated in vacuo. The crude material was purified by column chromatography on silica eluting with 0-50% EtOAc/petroleum ether to give the title compound (0.310 g). δH (CDCl3, 400 MHz) 7.12 (2H, d), 6.59 (2H, d), 4.15 (1H, m), 3.99 (1H, br.s), 3.78 (1H, d), 3.61 (2H, t), 3.40 (3H, s), 3.28 (3H, m), 3.08 (1H, td), 2.74 (1H, d), 2.58 (1H, d), 2.06 (1H, m), 1.94 (1H, m), 1.45 (9H, s), 1.21 (3H, d). MS (ES+): 264.2, no molecular ion (MH+) observed.

Workup

  1. customreaction mixture
  2. stirringstirred for a further 1 hour
  3. extractionThe aqueous layer was then extracted with DCM (×3)
  4. dry with materialthe combined organic layers were dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customThe crude material was purified by column chromatography on silica eluting with 0-50% EtOAc/petroleum ether

Sources & evidence

ORD record
ord-ca121e0941004f9dad6fa6d270a1e2a1
Source dataset
uspto-grants-2014_10
Patent number
US08853218B2

Reaction notes

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