2-Amino-2-methyl-1-propanol → 2-Amino-2-methyl-1-propanol

HRID 71015Notes

Reaction equation

HRID 71015 reaction equation
[CH3:1][CH:2]([C:4]1[N:8]([CH2:9][CH2:10][C@@H:11]([OH:19])[CH2:12][C@@H:13]([OH:18])[CH2:14][C:15]([OH:17])=[O:16])[C:7]([C:20]2[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=2)=[C:6]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:5]=1[C:33]([NH:35][C:36]1[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1)=[O:34])[CH3:3].[NH2:42][C:43]([CH3:47])([CH3:46])[CH2:44][OH:45]>C(#N)C>[CH3:3][CH:2]([C:4]1[N:8]([CH2:9][CH2:10][C@@H:11]([OH:19])[CH2:12][C@@H:13]([OH:18])[CH2:14][C:15]([OH:17])=[O:16])[C:7]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[C:6]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:5]=1[C:33]([NH:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:34])[CH3:1].[NH2:42][C:43]([CH3:47])([CH3:46])[CH2:44][OH:45].[CH3:3][CH:2]([C:4]1[N:8]([CH2:9][CH2:10][C@@H:11]([OH:19])[CH2:12][C@@H:13]([OH:18])[CH2:14][C:15]([OH:17])=[O:16])[C:7]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)=[C:6]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:5]=1[C:33]([NH:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)=[O:34])[CH3:1].[NH2:42][C:5]([CH3:6])([CH3:4])[CH2:33][OH:34]

Participants

6

Reactant 2

HCID 118072-Amino-2-methyl-1-propanolHCID 60823Atorvastatin2×

Product 3

HCID 118072-Amino-2-methyl-1-propanolHCID 60823AtorvastatinHCID 11541957Atorvastatin 2-amino-2-methylpropan-1-ol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent3×

Procedure

The 2-amino-2-methylpropan-1-ol salt of atorvastatin was synthesized by preparing a stock solution of the free acid of atorvastatin (U.S. Pat. No. 5,273,995) in acetonitrile (1 g in 40 mL of ACN). A solution of 2-amino-2-methylpropan-1-ol was prepared by dissolving 173.08 mg (1.1 equivalents) in acetonitrile (100 mL). The stock solution of atorvastatin free acid was added to the counterion solution with stirring. Seed crystals of the 2-amino-2-methylpropan-1-ol salt were added. Over time, additional acetonitrile was added to aid in stirring (100 mL), and the solid was allowed to stir. After 4 days of stirring at ambient temperature, the solids were isolated by vacuum filtration using a Buchner funnel fitted with a paper filter (#2 Whatman). The solids were rinsed with acetonitrile (75 mL), and placed in a 25° C. oven under nitrogen to dry for two days to afford atorvastatin 2-amino-2-methylpropan-1-ol.

Workup

  1. stirringin stirring (100 mL)
  2. stirringto stir
  3. stirringAfter 4 days of stirring at ambient temperature
  4. customthe solids were isolated by vacuum filtration
  5. customfitted with a paper
  6. filtrationfilter (#2 Whatman)
  7. washThe solids were rinsed with acetonitrile (75 mL)
  8. customplaced in a 25° C.
  9. customto dry for two days

Sources & evidence

ORD record
ord-e2d423d9d006489b940e715357376ebd
Source dataset
uspto-grants-2014_09
Patent number
US08822703B2

Reaction notes

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