Sodium borohydride → HCID 72709167, compound

HRID 1529245Notes

Reaction equation

HRID 1529245 reaction equation
[C:1]12([C:11]([N:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[C:16](=[O:23])[CH2:15][CH2:14]3)=[O:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[BH4-].[Na+]>CO>[C:1]12([C:11]([N:13]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[CH:16]([OH:23])[CH2:15][CH2:14]3)=[O:12])[CH2:2][CH:3]3[CH2:4][CH:5]([CH2:6][CH:7]([CH2:9]3)[CH2:8]1)[CH2:10]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 72709163HCID 72709163, compound

Product 1

HCID 72709167HCID 72709167, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 0.6 g (1.94 mmol) 1-(Adamantane-1-carbonyl)-2,3-dihydro-1H-quinolin-4-one and 0.11 g (2.91 mmol) NaBH4 in 20 mL methanol was stirred at room temperature. The mixture was evaporated, taken up on isolute and subjected to column chromatography on silica eluting with a gradient formed from heptane and TBME to yield after evaporation of the product containing fractions 0.557 g (92%) as white solid. MS(m/e): 312.4 (MH+).

Workup

  1. customThe mixture was evaporated
  2. customformed from heptane and TBME
  3. customto yield
  4. customafter evaporation of the product
  5. additioncontaining fractions 0.557 g (92%) as white solid

Sources & evidence

ORD record
ord-8f4b56a1cac34aa1889ef3862abf2e43
Source dataset
uspto-grants-2015_07
Patent number
US09090615B2

Reaction notes

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