Sodium borohydride → HCID 117778794, compound

HRID 1527066Notes

Reaction equation

HRID 1527066 reaction equation
[CH3:1][C:2]1[N:3]([CH:18]([C:20](=[O:22])[CH3:21])[CH3:19])[C:4]2[C:9]([C:10]=1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.[BH4-].[Na+]>C1COCC1.C(OCC)(=O)C>[OH:22][CH:20]([CH3:21])[CH:18]([N:3]1[C:4]2[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=2)[C:10]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[C:2]1[CH3:1])[CH3:19]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 89740097HCID 89740097, compound

Product 1

HCID 117778794HCID 117778794, compoundYield 93.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
31 °C

Procedure

To a solution of tert-butyl 2-methyl-1-(3-oxobutan-2-yl)-1H-indole-3-carboxylate (550 mg, 1.83 mmol) in THF (8 mL) was added NaBH4 (139 mg, 3.66 mmol) at 0° C. under N2. The reaction was stirred at 31° C. for 20 hrs. The mixture was diluted with ethyl acetate, washed with water and saturated aqueous NaHCO3. The organic layer was concentrated in vacuo to afford the title compound (520 mg) as a yellow oil which was used directly without purification.

Workup

  1. washwashed with water and saturated aqueous NaHCO3
  2. concentrationThe organic layer was concentrated in vacuo

Sources & evidence

ORD record
ord-cc657ab9ba0f4ab8bc3412f8ea9e27f9
Source dataset
uspto-grants-2015_07
Patent number
US09085583B2

Reaction notes

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