Sodium borohydride → HCID 53924158, compound

HRID 1459401Notes

Reaction equation

HRID 1459401 reaction equation
C[O:2][C:3](=O)[C:4]([CH2:25][C:26]1[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=1)([CH2:18][C:19]1[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=1)[C:5]([NH:7][C:8]12[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2)=[O:6].[BH4-].[Na+]>CO>[C:8]12([NH:7][C:5](=[O:6])[C:4]([CH2:3][OH:2])([CH2:18][C:19]3[CH:24]=[CH:23][N:22]=[CH:21][CH:20]=3)[CH2:25][C:26]3[CH:31]=[CH:30][N:29]=[CH:28][CH:27]=3)[CH2:9][CH:10]3[CH2:11][CH:12]([CH2:13][CH:14]([CH2:16]3)[CH2:15]1)[CH2:17]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 57147682HCID 57147682, compound

Product 1

HCID 53924158HCID 53924158, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a well-stirred solution of N-adamantan-1-yl-2,2-bis-pyridin4-ylmethyl-malonamic acid methyl ester (14.92 g, 34 mmol) in methanol (175 ml), sodium borohydride (6.50 g, 172 mmol) was added portionwise over 1 hour (ambient temperature). After stirring at ambient temperature for 18 hours, the solvent was removed in vacuo, and the residue was extracted with aqueous sodium bicarbonate/chloroform (300 ml of each). The aqueous layer was then extracted three times with equal volumes of chloroform. The combined organic extracts were concentrated in vacuo to an oil (13.55 g). Flash chromatography of the entire sample (silica gel, 40 micron mesh; elution with methanol/chloroform=4:96 in volume) afforded the (free base) title compound as an oil (7.9 g).

Workup

  1. customthe solvent was removed in vacuo
  2. extractionthe residue was extracted with aqueous sodium bicarbonate/chloroform (300 ml of each)
  3. extractionThe aqueous layer was then extracted three times with equal volumes of chloroform
  4. concentrationThe combined organic extracts were concentrated in vacuo to an oil (13.55 g)
  5. washFlash chromatography of the entire sample (silica gel, 40 micron mesh; elution with methanol/chloroform=4:96 in volume)

Sources & evidence

ORD record
ord-9bcd65ce0d7b4f698a606ece0a63d5b7
Source dataset
uspto-grants-1998_12
Patent number
US05854232

Reaction notes

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