Sodium cyanoborohydride → HCID 44828772, compound

HRID 564387Notes

Reaction equation

HRID 564387 reaction equation
Cl.[O:2]=[C:3]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=1)[CH2:4][NH:5][C:6]([C@@H:8]1[CH2:12][CH2:11][NH:10][CH2:9]1)=[O:7].O=[C:25]1[CH2:30][CH2:29][N:28]([C:31]2[CH:40]=[CH:39][C:34]([C:35]([O:37][CH3:38])=[O:36])=[CH:33][CH:32]=2)[CH2:27][CH2:26]1.[BH3-]C#N.[Na+]>CO>[CH3:38][O:37][C:35](=[O:36])[C:34]1[CH:33]=[CH:32][C:31]([N:28]2[CH2:29][CH2:30][CH:25]([N:10]3[CH2:11][CH2:12][C@@H:8]([C:6]([NH:5][CH2:4][C:3](=[O:2])[NH:13][C:14]4[CH:19]=[CH:18][CH:17]=[C:16]([C:20]([F:23])([F:21])[F:22])[CH:15]=4)=[O:7])[CH2:9]3)[CH2:26][CH2:27]2)=[CH:40][CH:39]=1

Participants

5

Reactant 3

HCID 5003444Sodium cyanoborohydrideHCID 57474997HCID 57474997, compoundHCID 67005165HCID 67005165, compound

Product 1

HCID 44828772HCID 44828772, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (3R)—N-(2-oxo-2-{[3-(trifluoromethyl)phenyl]amino}ethyl)pyrrolidine-3-carboxamide hydrochloride (130 mg, 0.370 mmol) in MeOH (1 mL) was added methyl 4-(4-oxopiperidin-1-yl)benzoate (95 mg, 0.407 mmol) and NaBH3CN (70 mg, 1.11 mmol). After overnight, the mixture was washed with EtOAc and NaHCO3 (sat. aq.), the organic phase was dried over MgSO4, concentrated, and subjected to flash chromatography (EtOAc) to generate the title compound as a white solid (45% yield, 2 steps). 1H-NMR (CDCl3) δ: 1.55-1.75 (m, 2H), 1.85-2.06 (m, 3H), 2.10-2.22 (m, 1H), 2.24-2.40 (m, 1H), 2.42-2.62 (m, 2H), 2.81-3.02 (m, 5H), 3.65-3.85 (m, 5H), 4.05-4.20 (m, 2H), 6.81 (d, J=8.9 Hz, 2H), 7.20-7.40 (m, 2H), 7.65-8.00 (m, 5H), 9.57 (s, 1H). MS m/z: 533 (M+1)

Workup

  1. washthe mixture was washed with EtOAc and NaHCO3 (sat. aq.)
  2. dry with materialthe organic phase was dried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-fd12dc2738d6448892a7aa6b2b38bc9e
Source dataset
uspto-grants-2011_11
Patent number
US08067457B2

Reaction notes

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