Lithium borohydride → [6-(3-Hydroxy-4-hydroxymethyl-pyrrolidin-1-yl)-6-oxo-hexyl]-carbamic Acid Benzyl Ester

HRID 20912

Reaction equation

HRID 20912 reaction equation
[BH4-].[Li+].C([O:5][C:6]([CH:8]1[CH:12]([OH:13])[CH2:11][N:10]([C:14](=[O:31])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][NH:20][C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[CH2:9]1)=O)C>O1CCCC1.CO.C(Cl)(Cl)Cl>[CH2:24]([O:23][C:21](=[O:22])[NH:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][C:14]([N:10]1[CH2:9][CH:8]([CH2:6][OH:5])[CH:12]([OH:13])[CH2:11]1)=[O:31])[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 2

HCID 4148881Lithium borohydrideHCID 686374701-(6-Benzyloxycarbonylamino-hexanoyl)-4-hydroxy-pyrrolidine-3-carboxylic Acid Ethyl Ester

Product 1

HCID 68637867[6-(3-Hydroxy-4-hydroxymethyl-pyrrolidin-1-yl)-6-oxo-hexyl]-carbamic Acid Benzyl Ester

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 21584188Chloroform methanolSolvent

Conditions

Temperature
0 °C

Procedure

To the solution of lithium borohydride (0.305 g, 13 mmol) in anhydrous tetrahydrofuran (25 mL) was added a solution of ethyl ester 62 (3.74 g, 9.2 mmol) in THF (25 mL) over a period of 30 mins at 0° C. After the addition the reaction mixture was brought to room temperature and stirred further under argon. The completion of the reaction was ascertained by TLC after 4 h. (Rf=0.4 in 10% MeOH/CHCl3). The reaction mixture was evaporated to dryness and cooled to 0° C. To the residue 3N HCl (40 mL) was added slowly. After stirring for 30 mins the product was extracted with dichloromethane (3×75 mL). The combined organic layer was washed with brine and dried over sodium sulfate. Organic layer was filtered and evaporated to dryness. Compound 63 was purified by column chromatography first by eluting with dichloromethane/methanol (5%) (3.2 g, 92%).

Workup

  1. additionAfter the addition the reaction mixture
  2. customwas brought to room temperature
  3. customThe reaction mixture was evaporated to dryness
  4. additionTo the residue 3N HCl (40 mL) was added slowly
  5. stirringAfter stirring for 30 mins the product
  6. extractionwas extracted with dichloromethane (3×75 mL)
  7. washThe combined organic layer was washed with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationOrganic layer was filtered
  10. customevaporated to dryness
  11. customCompound 63 was purified by column chromatography first
  12. washby eluting with dichloromethane/methanol (5%) (3.2 g, 92%)

Sources & evidence

ORD record
ord-f4aeb60b5ce44e79acb1c9a55e76f8e6
Source dataset
uspto-grants-2010_06
Patent number
US07745608B2

Linked notes

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