Sodium cyanoborohydride → HCID 86694485, compound

HRID 1519622Notes

Reaction equation

HRID 1519622 reaction equation
[F:1][C:2]([F:17])([F:16])[CH:3]1[NH:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1.[CH3:18][O:19][C:20]1[CH:27]=[C:26]([CH2:28][CH:29]=O)[CH:25]=[CH:24][C:21]=1[C:22]#[N:23].C([BH3-])#N.[Na+]>CO>[C:22]([C:21]1[CH:24]=[CH:25][C:26]([CH2:28][CH2:29][N:8]2[CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:13])([CH3:14])[CH3:15])=[O:10])[CH2:4][CH:3]2[C:2]([F:1])([F:16])[F:17])=[CH:27][C:20]=1[O:19][CH3:18])#[N:23]

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 665998503-Trifluoromethyl-piperazine-1-carboxylic acid tert-butyl esterHCID 772312592-(Methyloxy)-4-(2-oxoethyl)benzonitrile

Product 1

HCID 86694485HCID 86694485, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of tert-butyl 3-(trifluoromethyl)piperazine-1-carboxylate (72 mg, 0.28 mmol) and 2-methoxy-4-(2-oxoethyl)benzonitrile (50 mg, 0.28 mmol) in methanol (2.5 mL) at 0° C. was added sodium cyanoborohydride (25 mg, 0.40 mmol) and the mixture was stirred at room temperature for 12 hours. The reaction mixture was concentrated and purified by column chromatography (4->30% ethyl acetate:hexanes) to provide tert-butyl 4-[2-(4-cyano-3-methoxyphenyl)ethyl]-3-(trifluoromethyl)piperazine-1-carboxylate. LC-MS (IE, m/z): 414.4 [M+1]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by column chromatography (4->30% ethyl acetate:hexanes)

Sources & evidence

ORD record
ord-89aeaa4b2d56484db6fda6151953444d
Source dataset
uspto-grants-2015_07
Patent number
US09073882B2

Reaction notes

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