Sodium borohydride → HCID 57595461, compound

HRID 1785998Notes

Reaction equation

HRID 1785998 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C@H:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([C:22](=[O:31])[C:23]3[CH:28]=[CH:27][C:26]([C:29]#[N:30])=[CH:25][CH:24]=3)[C@@H:14]([CH3:32])[CH2:13]2)[C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.[BH4-].[Na+]>C(O)C.[Co](Cl)Cl>[NH2:30][CH2:29][C:26]1[CH:25]=[CH:24][C:23]([C:22]([N:15]2[C:16]3[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=3)[C@H:12]([N:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[C:9](=[O:11])[CH3:10])[CH2:13][C@@H:14]2[CH3:32])=[O:31])=[CH:28][CH:27]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 11662235HCID 11662235, compound

Product 1

HCID 57595461HCID 57595461, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 24288Cobalt(II) chlorideCatalystHCID 702EthanolSolvent

Procedure

N-{(2S,4R)-1-[4-(aminomethyl)benzoyl]-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl}-N-(4-chlorophenyl)acetamide was made following general procedure H, substituting 4-cyanobenzoyl chloride for 6-trifluoromethyl nicotinyl chloride. The rest of the procedure is followed as indicated in general procedure H to yield the corresponding nitrile, N-(4-chloro-phenyl)-N-[(2S,4R)-1-(4-cyano-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide. N-(4-Chloro-phenyl)-N-[(2S,4R)-1-(4-cyano-benzoyl)-2-methyl-1,2,3,4-tetrahydro-quinolin-4-yl]-acetamide (225 mg, 0.51 mmol) was dissolved in ethanol (7 mL) and cobalt dichloride (0.079 g, 0.61 mmol) and NaBH4 (0.059 g, 1.57 mmol) were added and the mixture was stirred at room temperature for 2 h. The slurry was filtered, concentrated, and subjected to flash chromatography (1% NH4OH, 15% MeOH, EtOAc) to yield the title compound (188 mg, 83%) as a white solid. 1H-NMR (CDCl3) δ: 1.00-1.20 (m, 1H), 1.14 (s, 3H), 1.48 (bs, 2H), 2.02 (s, 3H), 2.20-2.36 (m, 1H), 3.79 (s, 2H), 4.73-4.83 (m, 1H), 5.35-5.70 (m, 1H), 6.49 (d, 1H), 6.89 (t, 1H), 7.11-7.29 (m, 8H), 7.37 (d, 2H).

Workup

  1. filtrationThe slurry was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-93c98320a7f3439db997db72a95d930e
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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