Sodium cyanoborohydride → 3,3-diphenyl-1-{2-[7-(trifluoromethyl)-3,4-dihydroisoquinolin-2(1H)-yl]ethyl}pyrrolidin-2-one

HRID 1667140Notes

Reaction equation

HRID 1667140 reaction equation
Cl.[F:2][C:3]([F:15])([F:14])[C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][NH:10][CH2:11]2)=[CH:6][CH:5]=1.[O:16]=[C:17]1[C:21]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:20][CH2:19][N:18]1[CH2:34][CH:35]=O.C([BH3-])#N.[Na+]>CO>[C:28]1([C:21]2([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH2:20][CH2:19][N:18]([CH2:34][CH2:35][N:10]3[CH2:9][CH2:8][C:7]4[C:12](=[CH:13][C:4]([C:3]([F:2])([F:14])[F:15])=[CH:5][CH:6]=4)[CH2:11]3)[C:17]2=[O:16])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 441182867-(Trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline hydrochlorideHCID 866408362-(2-Oxo-3,3-diphenylpyrrolidin-1-yl)acetaldehyde

Product 1

HCID 674446003,3-diphenyl-1-{2-[7-(trifluoromethyl)-3,4-dihydroisoquinolin-2(1H)-yl]ethyl}pyrrolidin-2-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 7-(trifluoromethyl)-1,2,3,4-tetrahydroisoquinoline hydrochloride (0.153 g, 0.644 mmol), the product from Example 67B (0.120 g, 0.430 mmol) and sodium cyanoborohydride (0.040 g, 0.644 mmol) were stirred together in methanol (0.5 mL) at room temperature. After stirring overnight, the reaction was concentrated, dissolved in minimal dichloromethane and was loaded directly onto a SF15-12 column (Analogix®, Burlington, Wis.), and the title compound was eluted using a gradient of 5% to 100% ethyl acetate/hexanes over 20 minutes (flow=30 mL/minute). 1H NMR (300 MHz, CDCl3) δ ppm 7.36-7.42 (m, 1H), 7.29-7.34 (m, 4H), 7.18-7.26 (m, 2H), 7.12-7.18 (m, 6H), 3.66 (s, 2H), 3.63 (t, J=6.2 Hz, 2H), 3.44 (t, J=6.4 Hz, 2H), 2.69-2.84 (m, 8H); MS (ESI+) m/z 465 (M+H)+.

Workup

  1. concentrationthe reaction was concentrated
  2. dissolutiondissolved in minimal dichloromethane
  3. washthe title compound was eluted
  4. customover 20 minutes

Sources & evidence

ORD record
ord-231691fe3e61481dbcaac379e093633a
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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