Hydrochloric Acid → HCID 15671482, compound

HRID 2371398Notes

Reaction equation

HRID 2371398 reaction equation
[Cl-].[Ca+2].[Cl-].[BH4-].[Na+].C[O:7][C:8](=O)[C@@H:9]1[CH2:13][C@@H:12]([O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])[CH2:11][N:10]1[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23].Cl>C(O)C.O>[CH2:25]([O:24][C:22]([N:10]1[CH2:11][C@H:12]([O:14][Si:15]([C:18]([CH3:19])([CH3:20])[CH3:21])([CH3:17])[CH3:16])[CH2:13][C@H:9]1[CH2:8][OH:7])=[O:23])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 10069170HCID 10069170, compound

Product 1

HCID 15671482HCID 15671482, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

To a suspension of calcium chloride (53.55 g) in dry ethanol (455 ml), sodium borohydride (26.6 g) was added under nitrogen stream while ice-cooling, and the resultant suspension was stirred at the same temperature for 1 hour. A solution of trans-1-benzyloxycarbonyl-4-t-butyldimethylsilyloxy-L-proline methyl ester (68.87 g) in dry ethanol (200 ml) was added thereto while ice-cooling, and the resulting mixture was stirred at the same temperature for 1 hour and at 25° to 30° C. for 2 hours. The reaction mixture was neutralized with 6N hydrochloric acid, poured into water, extracted with ethyl acetate, washed with aqueous sodium chloride solution and dried over magnesium sulfate. Removal of the solvent gave (2S,4R)-1-benzyloxycarbonyl-2-hydroxymethyl-4-t-butyldimethylsilyloxypyrrolidine.

Workup

  1. additionwas added under nitrogen stream while ice-
  2. temperaturecooling
  3. temperaturewhile ice-cooling
  4. extractionextracted with ethyl acetate
  5. washwashed with aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customRemoval of the solvent

Sources & evidence

ORD record
ord-1b1ebe3449364a0aa6b8b1bb3ca93598
Source dataset
uspto-grants-1992_03
Patent number
US05093328

Reaction notes

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