Triethylamine → HCID 178451030, compound

HRID 2404103Notes

Reaction equation

HRID 2404103 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.[C:25]([O:29][C:30](=[O:35])[CH2:31][CH2:32][CH2:33][NH2:34])([CH3:28])([CH3:27])[CH3:26].C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl.ClCCl>[C:25]([O:29][C:30](=[O:35])[CH2:31][CH2:32][CH2:33][NH:34][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)([CH3:28])([CH3:26])[CH3:27]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 24750478Tert-butyl 4-aminobutanoate hydrochlorideHCID 866684126-(trans-4-Tert-butylcyclohexyloxy)-2-naphthaldehyde

Product 1

HCID 178451030HCID 178451030, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 6-(4-tert-butyl-cyclohexyloxy)-naphthalene-2-carbaldehyde (45 mg, 0.15 mmol, 4-amino-butyric acid tert-butyl ester HCl salt (115 mg, 0.59 mmol), and triethylamine (81 μL, 0.58 mmol) in 1,2-dichloroethane (1.5 mL) was treated with sodium triacetoxyborohydride (65 mg, 0.29 mmol). After stirring at room temperature over night, the mixture was diluted with dichloromethane and washed with aqueous sodium bicarbonate. The organic phase was dried over MgSO4, filtered and concentrated and residue was purified by silica gel column eluted with ethyl acetate in hexane from 0 to 100% to give colorless oil (33 mg, yield: 50%). ESI-MS: 454.4 (M+H)+; 1H NMR (400 MHz, CDCl3) δ=7.65-7.70 (m, 3H), 7.38-7.40 (dd, 1H), 7.10-7.14 (m, 2H), 4.22-4.28 (m, 1H), 3.90 (s, 2H), 2.67 (t, 2H), 2.28 (t, 4H), 1.89 (d, 2H), 1.81 (t, 2H), 1.40 (m, 1H), 1.42 (s, 9H), 1.30 (m, 4H), 0.9 (s, 9H).

Workup

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

Sources & evidence

ORD record
ord-f7d819ef2be447919266b486bf3da2b5
Source dataset
uspto-grants-2014_08
Patent number
US08802659B2

Reaction notes

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