Sodium cyanoborohydride → HCID 69272023, compound

HRID 751529Notes

Reaction equation

HRID 751529 reaction equation
C([BH3-])#N.[Na+].[C:5]([O:9][C:10](=[O:29])[N:11]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:21]=1[NH:20][CH:19]=[CH:18]2)([CH3:8])([CH3:7])[CH3:6]>C(O)(=O)C.C(OCC)(=O)C>[C:5]([O:9][C:10](=[O:29])[N:11]([CH2:22][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]2[C:21]=1[NH:20][CH2:19][CH2:18]2)([CH3:8])([CH3:6])[CH3:7]

Participants

5

Reactant 2

HCID 5003444Sodium cyanoborohydrideHCID 69267659HCID 69267659, compound

Product 1

HCID 69272023HCID 69272023, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add sodium cyanoborohydride (3.0 g, 47.6 mmol) to a solution of benzyl-(1H-indol-7-ylmethyl)carbamic acid tert-butyl ester (10.0 g, 29.8 mmol) in acetic acid. Stir the mixture at ambient temperature for 3 hours. Dilute with ethyl acetate and cool in an ice bath. Wash the mixture with aqueous 3.0 N sodium hydroxide until pH is 8. Dry the organic layer with magnesium sulfate and concentrate. Purify by chromatography (silica gel; hexane/ethyl acetate; 3:1 to 0:1) to afford a solid as the title compound (5.0 g, 50%). MS (ESI) m/z 339 (M+H)+.

Workup

  1. temperaturecool in an ice bath
  2. washWash the mixture with aqueous 3.0 N sodium hydroxide until pH is 8
  3. dry with materialDry the organic layer with magnesium sulfate
  4. concentrationconcentrate
  5. customPurify by chromatography (silica gel; hexane/ethyl acetate; 3:1 to 0:1)

Sources & evidence

ORD record
ord-56081235ba854302a16ca3f9811b7764
Source dataset
uspto-grants-2008_07
Patent number
US07405305B2

Reaction notes

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