Hydrochloric Acid → HCID 11099295, compound

HRID 975644Notes

Reaction equation

HRID 975644 reaction equation
[BH4-].[Na+].[Cl-].[Li+].[CH2:5]([N:12]1[CH2:16][C@H:15]([O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH2:14][C@H:13]1[C:25](OC)=[O:26])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.Cl.[OH-].[Na+].[Cl-].[Na+]>O1CCCC1.C(O)C>[CH2:5]([N:12]1[CH2:16][C@H:15]([O:17][Si:18]([C:21]([CH3:22])([CH3:23])[CH3:24])([CH3:20])[CH3:19])[CH2:14][C@H:13]1[CH2:25][OH:26])[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 14798Sodium HydroxideHCID 433294Lithium ChlorideHCID 4311764Sodium borohydrideHCID 53662624HCID 53662624, compound

Product 1

HCID 11099295HCID 11099295, compoundYield 101.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of sodium borohydride (16.2 g) and lithium chloride (18.1 g) in tetrahydrofuran (190 ml) were dropwise added (2S,4R)-1-benzyl-2-methoxycarbonyl-4-(t-butyldimethylsilyloxy)pyrrolidine (74.8 g) in tetrahydrofuran (190 ml), and ethanol (750 ml) under ice-cooling. The mixture was stirred at ambient temperature for 2 hours. The reaction mixture was cooled with dry ice-acetone bath and poured into ice-water. The mixture was adjusted to pH 6 with 1N hydrochloric acid and stirred for 10 minutes. The mixture was adjusted to pH 9~10 with 1N sodium hydroxide, and saturated with sodium chloride. After being extracted with ethyl acetate and tetrahydrofuran (1:1) three times, the organic layer was dried over anhydrous magnesium sulfate and evaporated in vacuo. To the residue was added chloroform. The chloroform layer was again dried over anhydrous magnesium sulfate, and evaporated in vacuo to give (2S,4R)-1-benzyl-2-hydroxymethyl-4-(t-butyldimethylsilyloxy)pyrrolidine (70.10 g).

Workup

  1. temperaturecooling
  2. temperatureThe reaction mixture was cooled with dry ice-acetone bath
  3. stirringstirred for 10 minutes
  4. extractionAfter being extracted with ethyl acetate and tetrahydrofuran (1:1) three times
  5. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  6. customevaporated in vacuo
  7. additionTo the residue was added chloroform
  8. dry with materialThe chloroform layer was again dried over anhydrous magnesium sulfate
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-0f3542e10f1b418aa4caa66f2d73515d
Source dataset
uspto-grants-1997_03
Patent number
US05608056

Reaction notes

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