Ammonium Hydroxide → HCID 69205275, compound

HRID 1374805Notes

Reaction equation

HRID 1374805 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH3:23])[CH2:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]3[O:22][CH2:21][CH2:20][C:18]3=2)[CH:13]=[CH:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([BH3-])#N.[Na+].[OH-].[NH4+]>C(O)(=O)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH3:23])[CH2:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]3[O:22][CH2:21][CH2:20][C:18]3=2)[CH2:13][CH2:12]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 14923Ammonium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 69205417HCID 69205417, compound

Product 1

HCID 69205275HCID 69205275, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a stirred solution/suspension of (S)-1-[2-(tert-butoxycarbonylamino)propyl]-7,8-dihydrofuro[2,3-g]indole (565 mg, 1.79 mmol) in acetic acid (40 mL) under Ar at 5° C. was added sodium cyanoborohydride (371 mg, 5.90 mmol) and the mixture was allowed to warm to ambient temperature and stir overnight. The resultant solution was poured onto ice-water (100 mL), basified (˜pH 8–9) by the addition of 30% ammonium hydroxide, and the resultant suspension was filtered and the solid washed with ice-cold water. The crude solid was purified by flash column chromatography [SiO2; ethyl acetate-heptane (3:7)] to afford the product (412 mg, 72%) as a white solid: mp 141–142.5° C.; Found: C, 67.87; H, 8.21; N, 8.80%. C18H26N2O3 requires: C, 67.90; H, 8.23; N, 8.79%.

Workup

  1. filtrationthe resultant suspension was filtered
  2. washthe solid washed with ice-cold water
  3. customThe crude solid was purified by flash column chromatography [SiO2; ethyl acetate-heptane (3:7)]

Sources & evidence

ORD record
ord-23d9ca34e27c4e1fb77f7c0b9783e38f
Source dataset
uspto-grants-2007_01
Patent number
US07166613B2

Reaction notes

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