Dimethyl Sulfide → Cbz-L-Prolinol

HRID 21766

反応式

HRID 21766 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].CSC>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

4

反応物 2

HCID 1068Dimethyl SulfideHCID 101987Benzyloxycarbonyl-L-proline

生成物 1

HCID 11096562Cbz-L-Prolinol収率 98%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

A 21.56 g (86.55 mmol) sample of the compound from step 24a above was dissolved in 200 mL of THF, and the solution was cooled to 0° C. BH3 -dimethyl sulfide (86.5 mL, 2N) was added dropwise under a nitrogen atmosphere. The reaction was stirred at room temperature for 16 hr, then cooled to 0° C. and quenched by careful addition of 10% acetic acid in methanol. The mixture was reduced in volume on a rotary evaporator, and the concentrate was dissolved in ethyl acetate, which was washed successively with 1N HCl, water and sodium bicarbonate solution. The organic extract was dried over Na2SO4 and concentrated to afford the title product, 19.94 g (98% yield).

後処理

  1. temperaturecooled to 0° C.
  2. customquenched by careful addition of 10% acetic acid in methanol
  3. customThe mixture was reduced in volume on a rotary evaporator
  4. dissolutionthe concentrate was dissolved in ethyl acetate
  5. washwhich was washed successively with 1N HCl, water and sodium bicarbonate solution
  6. extractionThe organic extract
  7. dry with materialwas dried over Na2SO4
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-b7584f1f3ebc4e52879c9f889abda715
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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