Ammonium Chloride → (S)-N-Boc-2-ethynylpyrrolidine

HRID 17173ノート

反応式

HRID 17173 の反応式
Br[C:2](Br)=[CH:3][C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].C([Li])(CC)C.[Cl-].[NH4+]>C1COCC1.CCOCC>[C:3]([C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])#[CH:2]

参加物

6

反応物 3

HCID 25517Ammonium ChlorideHCID 14730281(S)-t-butyl 2-(2,2-dibromovinyl)pyrrolidine-1-carboxylateHCID 178418400CID 53628100

生成物 1

HCID 11030701(S)-N-Boc-2-ethynylpyrrolidine

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

A solution of Example 538A (6.11 g, 17.21 mmol) in THF (150 mL) at −78° C. was treated with sec-butyl lithium (24.6 mL, 34.41 mmol) dropwise via syringe and stirred for 30 minutes at −78° C. The solution was then treated with a saturated ammonium chloride solution (100 mL), allowed to warm to room temperature, diluted with ether and extracted. The combined organic layers were washed with brine, dried (MgSO4) and concentrated to provide the desired product in quantitative yield. MS (ESI(+)) m/e 196 (M+H)+.

後処理

  1. temperatureto warm to room temperature
  2. extractionextracted
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-3b7925b1660d4f6187f302317a8f9746
出典データセット
uspto-grants-2010_06
特許番号
US07737160B2

反応ノート

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