6-Fluoro-1,2,3,4-tetrahydronaphthalen-2-one → HCID 11154195, compound

HRID 1353125Notes

Reaction equation

HRID 1353125 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][C:7](=O)[CH2:6][CH2:5]2.[CH:13]1([CH2:18][C:19]2[O:23][N:22]=[C:21]([NH:24][C:25](=[O:31])[C@@H:26]([NH2:30])[CH2:27][CH2:28][CH3:29])[CH:20]=2)[CH2:17][CH2:16][CH2:15][CH2:14]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl.C(O)(=O)C>[CH:13]1([CH2:18][C:19]2[O:23][N:22]=[C:21]([NH:24][C:25](=[O:31])[C@@H:26]([NH:30][CH:7]3[CH2:6][CH2:5][C:4]4[C:9](=[CH:10][CH:11]=[C:2]([F:1])[CH:3]=4)[CH2:8]3)[CH2:27][CH2:28][CH3:29])[CH:20]=2)[CH2:14][CH2:15][CH2:16][CH2:17]1

Participants

6

Reactant 3

HCID 50443856-Fluoro-1,2,3,4-tetrahydronaphthalen-2-oneHCID 5049666Sodium triacetoxyborohydrideHCID 86600866HCID 86600866, compound

Product 1

HCID 11154195HCID 11154195, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

6-Fluoro-3,4-dihydro-1H-naphthalen-2-one (0.2 mmol) was combined with 2-(S)-Amino-pentanoic acid (5-Cyclopentylmethyl-isoxazol-3-yl)-amide (0.2 mmol) in 2 mL of anhydrous dichloromethane under N2. Sodium triacetoxyborohydride (0.3 mmol) and two drops acetic acid were added and the reaction was stirred at rt for 16 h. The crude solution was then concentrated under reduced pressure and purified through flash chromatography on silica gel to give 2-(S)-(6-Fluoro-1,2,3,4-tetrahydro-naphthalen-2-ylamino)-pentanoic acid (5-cyclopentylmethyl-isoxazol-3-yl)-amide, LC-MS: retention time 2.0 min, M+1: 414.

Workup

  1. concentrationThe crude solution was then concentrated under reduced pressure
  2. custompurified through flash chromatography on silica gel

Sources & evidence

ORD record
ord-f4b95c68518240de9deaa117880dac70
Source dataset
uspto-grants-2007_05
Patent number
US07220865B2

Reaction notes

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