Methanol → HCID 23649128, compound

HRID 2267109Notes

Reaction equation

HRID 2267109 reaction equation
[CH3:1][N:2]([CH3:20])[C:3]([C:5]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:8]2([CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH2:7][CH:6]=1)=[O:4].O=[C:22]1[CH2:27][CH2:26][N:25]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:24][CH2:23]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CO>ClCCCl.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[CH3:1][N:2]([CH3:20])[C:3]([C:5]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:8]2([CH2:13][CH2:12][N:11]([CH:22]3[CH2:27][CH2:26][N:25]([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:24][CH2:23]3)[CH2:10][CH2:9]2)[CH2:7][CH:6]=1)=[O:4]

Participants

7

Reactant 4

HCID 887MethanolHCID 34767Ethyl 4-oxo-1-piperidinecarboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 59600645HCID 59600645, compound

Product 1

HCID 23649128HCID 23649128, compound

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 111,2-DichloroethaneSolvent

Procedure

A solution of N,N-dimethyl-2H-spiro[naphthalene-1,4′-piperidine]-4-carboxamide (B3) (33 mg, 0.13 mmol) and ethyl 4-oxopiperidine-1-carboxylate (60 mg, 0.35 mmol) in 1,2-dichloroethane (2 ml) was stirred at 40° C. for 5 h, followed by addition of titanium (IV) isopropoxide (0.05 ml, 0.17 mmol). The reaction mixture was stirred for 18 h and treated with sodium triacetoxyborohydride (50 mg, 0.23 mmol) for 24 h. Methanol (1 ml) was added and the reaction mixture was stirred for 1 h, evaporated and the residue was dissolved in methanol (1 ml) and purified by C-18 HPLC to give ethyl 4-(4-(dimethylcarbamoyl)-2H-spiro[naphthalene-1,4′-piperidine]-1′-yl)piperidine-1-carboxylate (Compound No. 4). LC-MS: m/e=426.3 (M+H). Rt=1.55 min. 1H-NMR (500 MHz, DMSO-d6): 9.32 (br. s, 1H), 7.39 (d, 1H), 7.34 (t, 1H), 7.26 (t, 1H), 6.95 (d, 1H), 5.97 (t, 1H), 4.12 (d, 2H), 4.05 (q, 2H), 4.04 (m, 2H), 3.43 (br. d, 2H), 3.22 (q, 2H), 2.98 (s, 3H), 2.81 (s, 3H), 2.80 (m, 1H), 2.56 (d, 2H), 2.14-2.07 (m, 4H), 1.92 (d, 2H), 1.56 (qd, 2H), 1.19 (t, 3H).

Workup

  1. stirringthe reaction mixture was stirred for 1 h
  2. customevaporated
  3. dissolutionthe residue was dissolved in methanol (1 ml)
  4. custompurified by C-18 HPLC

Sources & evidence

ORD record
ord-f6609d75844d477896ddcde8e07d66af
Source dataset
uspto-grants-2010_12
Patent number
US07858790B2

Reaction notes

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