Borane → HCID 14821719, compound

HRID 325245Notes

Reaction equation

HRID 325245 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:15][C@H:14]([O:16][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:13][C@H:9]1[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].B>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:15][C@H:14]([O:16][CH2:17][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH2:13][C@H:9]1[CH2:10][OH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6331BoraneHCID 11860409Boc-Hyp(Bzl)-OH

Product 1

HCID 14821719HCID 14821719, compoundYield 100.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of trans-N-t-butoxycarbonyl-4-benzyloxy-L-proline (3.32 g, 10.3 mmol) in 20 mL of THF was cooled in an ice/acetone bath and a solution of borane in THF (1M, 20.6 mL, 20.6 mrnmol) was added dropwise. The solution was stirred for 2 hours then the cooling bath was removed and the mixture stirred overnight. The reaction was quenched by the careful addition of water followed by the addition of 20 mL of 1N aqueous HCl and then poured into ethyl acetate. The layers were separated and the aqueous layer extracted with 2 portions of ethyl acetate. The combined organic extracts were 2M aqueous sodium carbonate, water and brine, dried, filtered and concentrated to provide 3.19 g (100%) of the title compound. MS (DCI, NH3): 308 (MH+).

Workup

  1. customthe cooling bath was removed
  2. stirringthe mixture stirred overnight
  3. customThe reaction was quenched by the careful addition of water
  4. additionfollowed by the addition of 20 mL of 1N aqueous HCl
  5. additionpoured into ethyl acetate
  6. customThe layers were separated
  7. extractionthe aqueous layer extracted with 2 portions of ethyl acetate
  8. customdried
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-76e30c9d64dc4ce09797782144fc8da9
Source dataset
uspto-grants-2001_04
Patent number
US06221865B1

Reaction notes

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