Sodium borohydride → HCID 117778794, compound

HRID 2206579Notes

Reaction equation

HRID 2206579 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-2400a501cf734f86b9857ee32949b511
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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