Phosphate → Cbz-L-Prolinol

HRID 1721079Notes

Reaction equation

HRID 1721079 reaction equation
[C:1]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13](O)=[O:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].P([O-])([O-])([O-])=O.CCOCC>C1COCC1>[C:1]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[CH2:13][OH:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

5

Reactant 3

HCID 1061PhosphateHCID 3283Diethyl EtherHCID 101987Benzyloxycarbonyl-L-proline

Product 1

HCID 11096562Cbz-L-ProlinolYield 113.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To Carbobenzyloxy-L-proline (Aldrich, 9.80 g, 39.3 mmol)in THF (100 mL) at 0° C. was added BH3 -THF complex (Aldrich, 1M in THF, 100 mL, 100 mmol). The mixture was stirred at 0° C. for 2 hours, then at ambient temperature for 16 hr. The reaction mixture was poured into pH 7 phosphate buffer solution (500 mL) and ether (600 mL) and mixed well. The layers were separated and the aqueous portion was extracted with ether (500 mL). The combined organic layers were washed with brine (500 mL),dried (Na2SO4) and filtered. The solvents were evaporated in vacuo leaving the crude carbobenzyloxy-L-prolinol as an oil (10.5 g).

Workup

  1. waitat ambient temperature for 16 hr
  2. additionmixed well
  3. customThe layers were separated
  4. extractionthe aqueous portion was extracted with ether (500 mL)
  5. washThe combined organic layers were washed with brine (500 mL),dried (Na2SO4)
  6. filtrationfiltered
  7. customThe solvents were evaporated in vacuo

Sources & evidence

ORD record
ord-774f4dc417e8439a8665d321d91120c3
Source dataset
uspto-grants-1996_04
Patent number
US05508418

Reaction notes

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