(2S,3R)-3-Hydroxypyrrolidine-2-carboxylic acid, N-BOC protected → Isoquinoline

HRID 346923ノート

反応式

HRID 346923 の反応式
C(N1CC[C@@H](O)[C@H]1C(O)=O)(OC(C)(C)C)=O.CC(C)([O-])C.[K+].Cl[C:24]1[C:33]2[C:28](=[CH:29][C:30](OC)=[CH:31][CH:32]=2)[CH:27]=[CH:26][N:25]=1>CS(C)=O>[CH:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26][N:25]=1

参加物

5

反応物 3

HCID 11096439(2S,3R)-3-Hydroxypyrrolidine-2-carboxylic acid, N-BOC protectedHCID 219010741-Chloro-6-methoxyisoquinolineHCID 23665647Potassium tert-butoxide

生成物 1

HCID 8405Isoquinoline収率 284.8%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
10 °C

実験手順

To a solution of N-BOC-3-(R)-hydroxy-L-proline (892 mg, 3.89 mmol) in DMSO (40 mL) at the ambient temperature was added potassium tert-butoxide (1.34 g, 12.0 mmol) in one portion. The formed suspension was stirred at this temperature for 30 min before being cooled to 10° C. 1-chloro-6-methoxy-isoquinoline (example 11, Step 2) (785 mg, 4.05 mmol) was added as solid in one portion and the final mixture was stirred at the ambient temperature for 12 h. Quenched with iced 5% citric acid (aq), extracted with EtOAC (100 mL). The aqueous phase was extracted with EtOAC again. The combined organic layers were washed with 5% citric acid (aq) and brine respectively, dried over MgSO4, filtered. The filtrate was evaporated in vacuo to dryness to yield 1.49 g (99%) of the desired product as an off-white foam. This material was used in the next step reaction as crude without further purification.

後処理

  1. customQuenched with iced 5% citric acid (aq)
  2. extractionextracted with EtOAC (100 mL)
  3. extractionThe aqueous phase was extracted with EtOAC again
  4. washThe combined organic layers were washed with 5% citric acid (aq) and brine respectively
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe filtrate was evaporated in vacuo to dryness

出典と根拠

ORDレコード
ord-2d5653aac1124276bdca55a1c0e1d034
出典データセット
uspto-grants-2007_02
特許番号
US07173004B2

反応ノート

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