Phosphate → Cbz-L-Prolinol

HRID 21760

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HRID 21760 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 11096562Cbz-L-Prolinol수율 113.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
0 °C

실험 절차

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).

후처리

  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)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customThe solvents were evaporated in vacuo

출처 및 근거

ORD 기록
ord-8f1e1fc265ee4e8686e00515ef1a9f73
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05424444

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