Tetrahydrofuran → N-{(S)-6-[(Isobutylmethylamino)methyl]-1,2,3,4-tetrahydronaphthalen-2-yl}-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide

HRID 1913811Notes

Reaction equation

HRID 1913811 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][C@@H:8]([NH:13][C:14](=[O:28])[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C@@H:23]3[CH2:27][CH2:26][CH2:25][O:24]3)=[CH:17][CH:16]=1)[CH2:7][CH2:6]2)=O.C1COCC1.[CH2:34]([NH:38][CH3:39])[CH:35]([CH3:37])[CH3:36].C([BH3-])#N.[Na+]>C(O)(=O)C.CO>[CH2:34]([N:38]([CH2:1][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][C@@H:8]([NH:13][C:14](=[O:28])[C:15]1[CH:20]=[CH:19][C:18]([O:21][CH2:22][C@@H:23]3[CH2:27][CH2:26][CH2:25][O:24]3)=[CH:17][CH:16]=1)[CH2:7][CH2:6]2)[CH3:39])[CH:35]([CH3:37])[CH3:36]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 12249N-MethylisobutylamineHCID 5003444Sodium cyanoborohydrideHCID 86762190N-((S)-6-formyl-1,2,3,4-tetrahydronaphthalen-2-yl)-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide

Product 1

HCID 59505857N-{(S)-6-[(Isobutylmethylamino)methyl]-1,2,3,4-tetrahydronaphthalen-2-yl}-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

To a mixture of N-((S)-6-formyl-1,2,3,4-tetrahydronaphthalen-2-yl)-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide (0.50 g), THF (5 ml), methanol (2 ml), isobutylmethylamine (0.23 g) and acetic acid (0.24 g) was added polymer-bound sodium cyanoborohydride (2.7 mmol), and the suspension was agitated at room temperature for 12 hours. The polymer was filtered off with suction and the filtrate was concentrated. The residue was purified by preparative HPLC. The product was thus obtained with the molecular weight of 450.63 (C28H38N2O3); MS (ESI): 451 (M+H+).

Workup

  1. filtrationThe polymer was filtered off with suction
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by preparative HPLC
  4. customThe product was thus obtained with the molecular weight of 450.63 (C28H38N2O3)

Sources & evidence

ORD record
ord-1233a39408ab49b29f2242c94b2fa111
Source dataset
uspto-grants-2013_12
Patent number
US08609731B2

Reaction notes

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