Borane → HCID 14821719, 화합물

HRID 325245노트

반응식

HRID 325245 반응식
[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]

참가 물질

4

반응물 2

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

생성물 1

HCID 14821719HCID 14821719, 화합물수율 100.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-76e30c9d64dc4ce09797782144fc8da9
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06221865B1

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