Methanol → HCID 59600599, compound

HRID 2267108Notes

Reaction equation

HRID 2267108 reaction equation
[NH:1]1[CH2:6][CH2:5][C:4]2([C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([C:16]#[N:17])=[CH:8][CH2:7]2)[CH2:3][CH2:2]1.[CH3:18][C:19]([CH3:24])([CH3:23])[CH2:20][CH:21]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].CO>ClCCCl>[CH3:18][C:19]([CH3:24])([CH3:23])[CH2:20][CH2:21][N:1]1[CH2:2][CH2:3][C:4]2([C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:9]([C:16]#[N:17])=[CH:8][CH2:7]2)[CH2:5][CH2:6]1

Participants

6

Reactant 4

HCID 887MethanolHCID 763353,3-DimethylbutanalHCID 5049666Sodium triacetoxyborohydrideHCID 59600612HCID 59600612, compound

Product 1

HCID 59600599HCID 59600599, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A solution of 2H-spiro[naphthalene-1,4′-piperidine]-4-carbonitrile (A4) (66 mg, 0.3 mmol), 3,3-dimethylbutanal (46 mg, 0.46 mmol) in 1,2-dichloroethane (5 ml) was stirred at 40° C. for 2 h. To the solution was added sodium triactoxyborohydride and the resulting mixture was stirred overnight, followed by treatment of MeOH (1 ml). Evaporation and the residue was dissolved in MeOH (2 ml) and purified by reverse phase C-18 HPLC to give 1′-(3,3-dimethylbutyl)-2H-spiro[naphthalene-1,4′-piperidine]-4-carbonitrile (Compound No. 51). LC-MS: m/e=309.1 (M+H). Rt=1.92 min. 1H-NMR (500 MHz, DMSO-d6): 9.03 (br. s, 1H), 7.49-7.40 (m, 4H), 7.12 (t, 1H), 3.45 (d, 2H), 3.22-3.11 (m, 4H), 2.78 (d, 2H), 2.03 (td, 2H), 1.88 (d, 2H), 1.58-1.54 (m, 2H), 0.92 (s, 9H).

Workup

  1. customEvaporation
  2. dissolutionthe residue was dissolved in MeOH (2 ml)
  3. custompurified by reverse phase C-18 HPLC

Sources & evidence

ORD record
ord-ea7cb14b534847a1bacefd5a9ccfd406
Source dataset
uspto-grants-2010_12
Patent number
US07858790B2

Reaction notes

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