Sodium borohydride → HCID 117778794, compound

HRID 2206557Notes

Reaction equation

HRID 2206557 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+]>O1CCCC1>[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

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 89740097HCID 89740097, compound

Product 1

HCID 117778794HCID 117778794, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of tert-butyl 2-methyl-1-(3-oxobutan-2-yl)-1H-indole-3-carboxylate (120 mg, 0.39 mmol) in tetrahydrofuran (3 mL) was added sodium borohydride (79 mg, 2.08 mmol). The reaction mixture was stirred at room temperature for 3 hours. The reaction mixture was quenched by adding water (3 ml) and extracted with ethyl acetate (20 mL×4). The combined organic layers was dried over sodium sulfate and concentrate to afford tert-butyl 1-(3-hydroxybutan-2-yl)-2-methyl-1H-indole-3-carboxylate (110 mg, yield: 93%) as a yellow oil. LRMS (M+H+) m/z: calcd 303.17. found 304.

Workup

  1. customThe reaction mixture was quenched
  2. additionby adding water (3 ml)
  3. extractionextracted with ethyl acetate (20 mL×4)
  4. dry with materialThe combined organic layers was dried over sodium sulfate
  5. concentrationconcentrate

Sources & evidence

ORD record
ord-6fa3a91ac5ca4cfb9be635b9ef0760ef
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

Loading…