Tetrahydrofuran → HCID 18940470, compound

HRID 355677Notes

Reaction equation

HRID 355677 reaction equation
O1CCCC1.C(O[C:14]([NH:16][CH:17]([CH:25]([OH:37])[C:26]1[S:27][C:28]([CH2:31][N:32]2[CH2:36][CH2:35][CH2:34][CH2:33]2)=[CH:29][CH:30]=1)[C:18](OC(C)(C)C)=[O:19])=O)C1C=CC=CC=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1.CCOCC.CCOCC.CO>[NH3:16].[CH3:14][NH:16][CH:17]([CH2:18][OH:19])[CH:25]([C:26]1[S:27][C:28]([CH2:31][N:32]2[CH2:36][CH2:35][CH2:34][CH2:33]2)=[CH:29][CH:30]=1)[OH:37]

Participants

8

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 18940426HCID 18940426, compoundHCID 21226445Aluminium lithium hydride2×

Product 2

HCID 222AmmoniaHCID 18940470HCID 18940470, compoundYield 116.4%

Reagents, catalysts & solvents 2

HCID 21864698Diethyl ether methanolSolventHCID 21868444Ether tetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

A tetrahydrofuran solution (10 ml) of 1.2 g of t-butyl 2-benzyloxycarbonylamino-3-hydroxy-3-[5-(1-pyrrolidinyl)methyl-2-thienyl]propionate (A form) was added dropwise to 500 mg of lithium aluminum hydride in tetrahydrofuran:ether (1:1) mixed solution (50 ml) in an ice bath, and the resulting mixture was stirred for 2 hours under reflux at 50° C. Excess lithium aluminum hydride was decomposed with ether:methanol (4:1) mixed solution, and the resulting solution was mixed with 1N sodium hydroxide aqueous solution (2.5 ml) and the mixture was stirred overnight. After removing the insoluble materials by filtration, the resulting filtrate was evaporated under reduced pressure, and the thus obtained residue was subjected to silica gel column chromatography and elution was carried out with chloroform:methanol (20:1) and (10:1) and chloroform:methanol:concentrated aqueous ammonia (200:20:1) and (100:10:1) in that order to obtain 410 mg of 2-methylamino-1-[5-(1-pyrrolidinyl)methyl-2-thienyl]propane-1,3-diol (A form).

Workup

  1. additionmixed solution
  2. stirringthe mixture was stirred overnight
  3. customAfter removing the insoluble materials
  4. filtrationby filtration
  5. customthe resulting filtrate was evaporated under reduced pressure
  6. washthe thus obtained residue was subjected to silica gel column chromatography and elution

Sources & evidence

ORD record
ord-2c97107e4e0d4624b161ad7370a04757
Source dataset
uspto-grants-1998_11
Patent number
US05834460

Reaction notes

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