Sodium borohydride → HCID 58530016, compound

HRID 451289Notes

Reaction equation

HRID 451289 reaction equation
[CH2:1]([O:8][NH:9][C@H:10]1[CH2:14][N:13](C(=O)C(F)(F)F)[C@H:12]([C:21]([O:23][CH2:24][CH:25]=[CH2:26])=[O:22])[CH2:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[CH2:1]([O:8][NH:9][C@H:10]1[CH2:14][NH:13][C@H:12]([C:21]([O:23][CH2:24][CH:25]=[CH2:26])=[O:22])[CH2:11]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 58530111HCID 58530111, compound

Product 1

HCID 58530016HCID 58530016, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of allyl (4R)-4-[(benzyloxy)amino]-1-(trifluoroacetyl)-L-prolinate (1.19 g, 3.20 mmol) in methanol (9.5 mL) was added slowly to a solution of sodium borohydride (312 mg, 8.25 mmol) in methanol (9.5 mL) at −10° C. The reaction mixture was allowed to warm to 0° C. slowly then stirred at 0° C. for 3 hours. Additional sodium borohydride (0.29 g, 7.67 mmol) was added at 0° C. and the reaction mixture was stirred at 0° C. for three hours then silica gel (to pre-absorb the crude product for chromatography) was added and the solvent removed under vacuum. The residue was chromatographed on silica gel eluted with 15:9:1 dichloromethane:ethyl acetate:methanol to afford the title compound as a colorless oil.

Workup

  1. stirringthe reaction mixture was stirred at 0° C. for three hours
  2. customsilica gel (to pre-absorb the crude product for chromatography)
  3. additionwas added
  4. customthe solvent removed under vacuum
  5. customThe residue was chromatographed on silica gel
  6. washeluted with 15:9:1 dichloromethane

Sources & evidence

ORD record
ord-75ef66c1f981423a842883b4e629c2f2
Source dataset
uspto-grants-2013_07
Patent number
US08487093B2

Reaction notes

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