Sodium borohydride → HCID 70291348, compound

HRID 850368Notes

Reaction equation

HRID 850368 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]1[CH2:11][C:12]([N:14]1[C@H:18]([C:19]([N:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[O:20])[CH2:17][S:16][CH2:15]1)=[O:13].[BH4-].[Na+]>CO>[OH:1][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][CH:3]1[CH2:11][C:12]([N:14]1[C@H:18]([C:19]([N:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)=[O:20])[CH2:17][S:16][CH2:15]1)=[O:13]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 70289412HCID 70289412, compound

Product 1

HCID 70291348HCID 70291348, compoundYield 108.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolved in 20 ml of methanol were 500 mg of 3-(1-oxo-2-indanacetyl)-4-(R)-(1-pyrrolidinecarbonyl) thiazolidine, and 80 mg of NaBH4 were added to the solution. After stirring the mixture at room temperature, the resultant liquid reaction mixture was concentrated under reduced pressure, and the residue was added with water and extracted with chloroform. After the extract was dried over anhydrous magnesium sulfate, chloroform was distilled off under reduced pressure to obtain 545 mg of 3-(1-hydroxy-2-indanacetyl)-4-(R)-(1-pyrrolidinecarbonyl)thiazolidine. Thereafter, the process was allowed to progress in accordance with the process of Synthetic Example 1, thereby obtaining the title compound as a diastereomeric mixture. Yield: 87% (amorphous).

Workup

  1. additionwere added to the solution
  2. customthe resultant liquid reaction mixture
  3. concentrationwas concentrated under reduced pressure
  4. additionthe residue was added with water
  5. extractionextracted with chloroform
  6. dry with materialAfter the extract was dried over anhydrous magnesium sulfate, chloroform
  7. distillationwas distilled off under reduced pressure

Sources & evidence

ORD record
ord-78b2146dae3e42efb86e5aab08fb88af
Source dataset
uspto-grants-2000_01
Patent number
US06017929

Reaction notes

Loading…