Sodium cyanoborohydride → HCID 23400512, compound

HRID 2252739Notes

Reaction equation

HRID 2252739 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH3:24])[CH2:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]3=2)[CH:13]=[CH:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([BH3-])#N.[Na+]>C(O)(=O)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH3:24])[CH2:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]3[CH:23]=[CH:22][CH:21]=[CH:20][C:18]3=2)[CH2:13][CH2:12]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 69207073HCID 69207073, compound

Product 1

HCID 23400512HCID 23400512, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution of (S)-1-[2-(tert-butoxycarbonylamino)propyl]-benz[g]indole (0.49 g, 1.5 mmol) in acetic acid (10 mL) was added portionwise sodium cyanoborohydride (95%, 0.30 g, 4.5 mmol). The mixture was stirred for 16 h and partitioned between ether (40 mL) and saturated aqueous sodium bicarbonate solution (3×50 mL). The organic layer was washed with brine (2×), dried (magnesium sulfate), concentrated in vacuo and purified by column chromatography [SiO2; heptane-ethyl acetate (6:1)] to give the product (0.24 g, 49%) as a pale yellow solid: IR νmax (Nujol)/cm−1 1689, 1528, 1362, 1298, 1051 and 790; NMR δH (400 MHz, CDCl3) 1.39 (3H, d, J 6.5 Hz), 1.45 (9H, s), 3.11-3.28 (2H, m), 3.32-3.42 (2H, m), 3.62-3.69 (2H, m), 3.98-4.08 (1H, m), 4.78 (1H, brs), 7.30-7.38 (1H, m), 7.33-7.41 (3H, m), 7.72-7.81 (1H, m) and 7.98-8.01 (1H, m).

Workup

  1. custompartitioned between ether (40 mL) and saturated aqueous sodium bicarbonate solution (3×50 mL)
  2. washThe organic layer was washed with brine (2×)
  3. dry with materialdried (magnesium sulfate)
  4. concentrationconcentrated in vacuo
  5. custompurified by column chromatography [SiO2; heptane-ethyl acetate (6:1)]

Sources & evidence

ORD record
ord-fdd1075ff28f493b9f946c7d1d17a741
Source dataset
uspto-grants-2008_01
Patent number
US07323473B2

Reaction notes

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