Hydrochloric Acid → (R)-[1-(2-hydroxy-ethyl)-4,5,6,7-tetrahydro-1H-indazol-4-yl]-carbamic acid benzyl ester

HRID 2387529ノート

反応式

HRID 2387529 の反応式
C([O:3][C:4](=O)[CH2:5][N:6]1[C:14]2[CH2:13][CH2:12][CH2:11][C@@H:10]([NH:15][C:16]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[O:17])[C:9]=2[CH:8]=[N:7]1)C.[BH4-].[Na+].Cl>CO>[CH2:19]([O:18][C:16](=[O:17])[NH:15][C@@H:10]1[CH2:11][CH2:12][CH2:13][C:14]2[N:6]([CH2:5][CH2:4][OH:3])[N:7]=[CH:8][C:9]1=2)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 4311764Sodium borohydrideHCID 59152896((R)-4-benzyloxycarbonylamino-4,5,6,7-tetrahydro-indazol-1-yl)-acetic acid ethyl ester

生成物 1

HCID 59152899(R)-[1-(2-hydroxy-ethyl)-4,5,6,7-tetrahydro-1H-indazol-4-yl]-carbamic acid benzyl ester収率 95.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
70 °C

実験手順

To a solution of ((R)-4-benzyloxycarbonylamino-4,5,6,7-tetrahydro-indazol-1-yl)-acetic acid ethyl ester (2.00 g, 5.60 mmol) in methanol (150 mL) was added sodium borohydride (1.61 g, 39.5 mmol). The mixture was stirred at 70° C. for 2 hours. After being cooled to room temperature, the reaction mixture was acidified to pH 7 with 5N hydrochloric acid, and then concentrated to remove methanol. The resulting mixture was extracted with dichloromethane (20 mL). After filtering out any insoluble materials from the organic layer, the filtrate was concentrated in vacuo to give (R)-[1-(2-hydroxy-ethyl)-4,5,6,7-tetrahydro-1H-indazol-4-yl]-carbamic acid benzyl ester (1.68 g, 95%) as a white solid. MS calcd. for C17H21N3O3 315, obsd. (ESI+) [(M+H)+] 316.

後処理

  1. temperatureAfter being cooled to room temperature
  2. concentrationconcentrated
  3. customto remove methanol
  4. extractionThe resulting mixture was extracted with dichloromethane (20 mL)
  5. filtrationAfter filtering out any insoluble materials from the organic layer
  6. concentrationthe filtrate was concentrated in vacuo

出典と根拠

ORDレコード
ord-6b933b4625f14f81b91cc6dbd9e8eae1
出典データセット
uspto-grants-2012_09
特許番号
US08268870B2

反応ノート

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