Aluminium lithium hydride → HCID 70200310、化合物

HRID 861353ノート

反応式

HRID 861353 の反応式
C[O:2][C:3]([CH2:5][C:6]1[CH:29]=[CH:28][C:9]([O:10][CH2:11][C@@H:12]2[CH2:27][N:15]3[CH2:16][CH2:17][N:18]([C:20]4[N:25]=[CH:24][C:23]([F:26])=[CH:22][N:21]=4)[CH2:19][C@@H:14]3[CH2:13]2)=[CH:8][CH:7]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[OH:2][CH2:3][CH2:5][C:6]1[CH:29]=[CH:28][C:9]([O:10][CH2:11][C@@H:12]2[CH2:27][N:15]3[CH2:16][CH2:17][N:18]([C:20]4[N:21]=[CH:22][C:23]([F:26])=[CH:24][N:25]=4)[CH2:19][C@@H:14]3[CH2:13]2)=[CH:8][CH:7]=1

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 57016126HCID 57016126、化合物

生成物 1

HCID 70200310HCID 70200310、化合物収率 63%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

実験手順

A solution of 0.13 g (0.33 mmol) of (7S,8aS)-7-(4-((methoxycarbonyl)methyl)phenoxy)methyl-2-(5-fluoropyrimidin-2-yl)-1,2,3,4,6,7,8,8a-octahydro-pyrrolo[1,2-a]pyrazine (Example 11i) in 15 mL of anhydrous ethyl ether was added dropwise to an ice-cold suspension of 0.025 g (0.65 mmol) of lithium aluminum hydride in 15 mL of anhydrous ethyl ether and the mixture stirred for 30 min. The reaction was carefully quenched at 0° C. with 0.025 mL of water, 0.025 mL of 15% sodium hydroxide, and 0.075 mL of water. The precipiate which formed was filtered through Celite, the filtrate concentrated in vacuo, and purification of the residue by flash silica gel chromatography with 95:5 ethyl acetate:methanol gave 0.075 g (63%) of the title compound. mp (.HCl) 145°-147° C. HRMS calcd for C20H26FN4 O2 (MH+): 373.2040, found: 373.2054.

後処理

  1. customThe reaction was carefully quenched at 0° C. with 0.025 mL of water, 0.025 mL of 15% sodium hydroxide, and 0.075 mL of water
  2. customThe precipiate which formed
  3. filtrationwas filtered through Celite
  4. concentrationthe filtrate concentrated in vacuo, and purification of the residue by flash silica gel chromatography with 95:5 ethyl acetate

出典と根拠

ORDレコード
ord-12b82b0127504299966061e250f6691f
出典データセット
uspto-grants-1998_02
特許番号
US05714487

反応ノート

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