Acetic Acid → HCID 178463667, compound

HRID 713911Notes

Reaction equation

HRID 713911 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]([CH:22]=O)[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].[CH2:24]([NH2:26])[CH3:25].CC(O)=O.[BH3-]C#N.[Na+]>C(Cl)Cl>[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]([CH2:22][NH:26][CH2:24][CH3:25])[CH:16]=[CH:15]3)[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6341EthylamineHCID 5003444Sodium cyanoborohydrideHCID 178445787HCID 178445787, compound

Product 1

HCID 178463667HCID 178463667, compoundYield 115.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6-((trans)-4-tert-butylcyclohexyloxy)-2-naphthaldehyde (200 mg, 0.64 mmol, 1 equiv), ethanamine (58 mg, 1.05 mmol, 2 equiv) and AcOH (62 mg, 1.05 mmol, 2 equiv) were dissolved in DCM (15 mL), and the mixture was stirred at r.t. for 2 h. Then NaBH3CN (101 mg, 1.9 mmol, 3 equiv) was added to the mixture and stirred for 16 h at r.t. The reaction mixture was washed by brine, dried over Na2SO4, and concentrated to give the title compound as a gray oil (250 mg, 100%). ESI-MS (M+1)+: 340.3. 1H NMR (400 MHz, CDCl3) δ: 7.73˜7.63 (m, 3H), 7.42˜7.31 (m, 1H), 7.16˜7.09 (m, 2H), 4.30˜4.21 (m, 1H), 3.91 (s, 2H), 2.73 (q, 2H), 2.31˜2.23 (m, 2H), 1.93˜1.83 (m, 2H), 1.49˜1.36 (m, 2H), 1.27˜1.18 (m, 2H), 1.15 (t, 3H), 1.12˜1.05 (m, 1H), 0.89 (s, 9H).

Workup

  1. stirringstirred for 16 h at r.t
  2. washThe reaction mixture was washed by brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-435af79d095e4058aa2888cf64c7840c
Source dataset
uspto-grants-2015_11
Patent number
US09186367B2

Reaction notes

Loading…