Phosphate → Cbz-L-Prolinol

HRID 21760

反応式

HRID 21760 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

HCID 11096562Cbz-L-Prolinol収率 113.6%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8f1e1fc265ee4e8686e00515ef1a9f73
出典データセット
uspto-grants-1995_06
特許番号
US05424444

関連ノート

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