Ammonia → HCID 69269014, compound

HRID 751509Notes

Reaction equation

HRID 751509 reaction equation
C[O:2][C:3](=O)[C:4]([C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([CH:15]2[CH2:20][CH2:19][N:18]([CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH2:17][CH2:16]2)[CH:7]=1)=[O:5].CO.[BH4-].[Na+].[NH3:33]>>[CH2:21]([N:18]1[CH2:17][CH2:16][CH:15]([N:8]2[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[C:6]([CH:4]([OH:5])[C:3]([NH2:33])=[O:2])=[CH:7]2)[CH2:20][CH2:19]1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 4

HCID 222AmmoniaHCID 887MethanolHCID 4311764Sodium borohydrideHCID 69269504HCID 69269504, compound

Product 1

HCID 69269014HCID 69269014, compoundYield 103%

Procedure

Dissolve [1-(1-benzylpiperidin-4-yl)-1H-indol-3-yl]oxoacetic acid methyl ester (1.29 g, 3.43 mmol) in 2 M ammonia: methanol (35 mL) and stir at room temperature under nitrogen for 1.5 hours. Concentrate to a white solid and slurry into absolute ethanol (40 mL). Add sodium borohydride (0.65 g, 5 equiv) and stir 3 hours at room temperature under nitrogen. Concentrate then dilute with ethyl acetate and quench with water. Wash organic layer with brine. Dry over magnesium sulfate, filter and concentrate to give crude product (1.28 g, 103%). MS (ES, m/z): 364.2 (M+1).

Workup

  1. concentrationConcentrate to a white solid and slurry into absolute ethanol (40 mL)
  2. concentrationConcentrate
  3. additionthen dilute with ethyl acetate
  4. customquench with water
  5. dry with materialDry over magnesium sulfate
  6. filtrationfilter
  7. concentrationconcentrate

Sources & evidence

ORD record
ord-4160490ffccd4b0eb16b03d575d919a7
Source dataset
uspto-grants-2008_07
Patent number
US07405305B2

Reaction notes

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