Propanal → (R)-3-(N-Cyclohexyl-N-n-propylamino)-8-fluoro-5-methoxy-3,4-dihydro-2H-1-benzopyran

HRID 52283Notes

Reaction equation

HRID 52283 reaction equation
[CH:1]1([NH:7][C@@H:8]2[CH2:13][C:12]3[C:14]([O:19][CH3:20])=[CH:15][CH:16]=[C:17]([F:18])[C:11]=3[O:10][CH2:9]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH:21](=O)[CH2:22][CH3:23].[BH3-]C#N.[Na+]>CO>[CH:1]1([N:7]([C@@H:8]2[CH2:13][C:12]3[C:14]([O:19][CH3:20])=[CH:15][CH:16]=[C:17]([F:18])[C:11]=3[O:10][CH2:9]2)[CH2:21][CH2:22][CH3:23])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 527PropanalHCID 5003444Sodium cyanoborohydrideHCID 54309583(R)-3-(N-Cyclohexylamino)-8-fluoro-5-methoxy-3,4-dihydro-2H-1-benzopyran

Product 1

HCID 54052643(R)-3-(N-Cyclohexyl-N-n-propylamino)-8-fluoro-5-methoxy-3,4-dihydro-2H-1-benzopyranYield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the solution of (R)-3-(N-cyclohexylamino)-8-fluoro-5-methoxy-3,4-dihydro-2H-1-benzopyran in methanol (25 mL) were propanal (1.3 g, 23 mmol) and NaCNBH3 (0.15 g, 2.3 mmol) added. The solution was stirred overnight to give the desired compound in a 97% yield according to GC. The solvent was removed in vacuo and the residue was worked up by extraction to give 0.7 g of the title compound as a colorless oil. GC/MS (70 eV) M=321 (40%).

Workup

  1. additionadded

Sources & evidence

ORD record
ord-81ade117237a4afe9b0ca1ca27f726d5
Source dataset
uspto-grants-1997_04
Patent number
US05616610

Reaction notes

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