Triethylamine → HCID 178472684, compound

HRID 713885Notes

Reaction equation

HRID 713885 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](=[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].Cl.[CH2:25]([O:27][C:28](=[O:31])[CH2:29][NH2:30])[CH3:26].C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.ClCCl>[CH2:25]([O:27][C:28](=[O:31])[CH2:29][NH:30][CH2:22][C:17]1[CH:16]=[CH:15][C:14]2[C:19](=[CH:20][CH:21]=[C:12]([O:11][C@H:8]3[CH2:9][CH2:10][C@H:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH2:6][CH2:7]3)[CH:13]=2)[CH:18]=1)[CH3:26]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 2723640Glycine ethyl ester, hydrochlorideHCID 5049666Sodium triacetoxyborohydrideHCID 866684126-(trans-4-Tert-butylcyclohexyloxy)-2-naphthaldehyde

Product 1

HCID 178472684HCID 178472684, compoundYield 55.5%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 6-(4-tert-butyl-cyclohexyloxy)-naphthalene-2-carbaldehyde (90 mg, 0.29 mmol), glycine ethyl ester hydrochloride (162 mg, 1.16 mmol), and triethylamine (0.16 mL, 1.16 mmol) in 1,2-dichloroethane (2 mL) was treated with sodium triacetoxyborohydride (129 mg, 0.58 mmol). The mixture was stirred at room temperature overnight. The solution was diluted with dichloromethane and washed with aqueous sodium bicarbonate. The organic phase was dried over MgSO4 and concentrated. The residue was purified with a silica gel column eluted with ethyl acetate in hexane from 0 to 100% to give product (64 mg, yield: 55%). ESI-MS: 420.30 (M+23)+; 1H NMR (400 MHz, CDCl3) δ=7.66-7.70 (m, 3H), 7.41 (dd, 1H), 7.11-7.14 (m, 2H), 4.26 (m, 1H), 4.19 (q, 2H), 3.93 (s, 2H), 3.43 (s, 2H), 2.28 (d, 4H), 1.89 (d, 2H), 1.44 (q, 2H), 1.27 (t, 3H), 1.09-1.20 (m, 3H), 0.89 (s, 9H).

Workup

  1. washwashed with aqueous sodium bicarbonate
  2. dry with materialThe organic phase was dried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified with a silica gel column
  5. washeluted with ethyl acetate in hexane from 0 to 100%

Sources & evidence

ORD record
ord-e430a979aab14d79bfa3868ec09a0772
Source dataset
uspto-grants-2015_11
Patent number
US09186367B2

Reaction notes

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